MXPA03005668A

MXPA03005668A - Macrolide antibiotics.

Info

Publication number: MXPA03005668A
Application number: MXPA03005668A
Authority: MX
Inventors: Tibasco Jessica
Original assignee: Pliva D D
Priority date: 2000-12-21
Filing date: 2001-12-20
Publication date: 2004-12-03
Also published as: CA2432429A1; AR042583A1; AU1727702A; ATE345350T1; HUP0302526A2; JP2004531471A; EP1363925A1; US20040077557A1; EP1363925B1; AU2002217277B2; US20060211636A1; DE60124594T2; KR20030068189A; CZ20031751A3; BR0116431A; PL365012A1; ES2275621T3; NZ526450A; DE60124594D1; CN1492874A

Abstract

The present invention relates to 11,12 ggr; lactone ketolides of formula (I) wherein R, R1, R2, R3 are as defined herein and pharmaceutically acceptable salts and solvates thereof, to process for their preparation and their use in therapy or prophylaxis of systemic or topical bacterial infections in a human or animal body.

Description

MACROLIDOS DESCRIPTIVE MEMORY The present invention relates to novel semi-synthetic macropiides having antibacterial activity. More particularly, the invention relates to 1 1, 12? lactone, to procedures for its preparation, to compounds that contain them, and to its use in medicine. EP 1 114826 generically discloses, among others, macromoidal compounds of formula (A) having antibacterial activity. wherein R-i is hydrogen or a hydroxyl protecting group; f¾ is, inter alia, an optionally substituted C 10 alkyl, X is, inter alia, oxygen, X 2 is, inter alia, CH 2, Y is NH, O or S, R 5 is, inter alia, C (O), and R13 is hydrogen or halo. The inventors have now found ketones of 11, 12? novel lactones, which have antibacterial activity.

In this way, the present invention provides compounds of the general formula (I): wherein: R is hydrogen, cyano, (CH2) nA-X-R4 or (CH2) nR5; A is a group selected from -N (R6) -, -N [C (0) R6] -, -N (R6) C (0) -, -N (R6) S (0) 2-, -N ( R6) C (0) 0-, -N = C (R6) - or -N (R6) C (Y) N (R7) -; R- \ is C1_6alkyl or C3_6alkenyl; R2 is hydrogen or a hydroxyl protecting group; R3 is hydrogen or halogen; X is a bond, an alkylene chain of C 1, a C2-10 alkenylene chain or a C2-10 alkynylene chain, wherein said chains are: i) optionally interrupted by a bivalent radical selected from -O-, - N (R8) -, -C (O) -, -N (R8) C (Y) N (Rg) -, -S (0) m-, -N (R8) C (0) -, -C (0) N (R8) -, -N (R8) C (0) C (0) -, -C (0) 0- or -C (NOR6) - and / or ii) optionally substituted by one or two groups selected from: C-1,4 alkyl, oxo, Ci_ alkoxy, halogen, cyano, phenoxy, hydroxy, NR8Rg, N (R8) C (0) Rg, = NOR6, NR8C (Y) NRg or optionally substituted phenyl; R is selected from: hydrogen, optionally substituted phenyl, optionally substituted C3-7 cycloalkyl, optionally substituted 9 to 10 membered bicyclic carbocyclic, optionally substituted 5 or 6 membered heteroaryl, wherein the 5-membered heteroaryl contains at least a heteroatom selected from oxygen, sulfur or nitrogen, and the 6-membered heteroaryl group contains from 1 to 3 nitrogen atoms, optionally substituted 5 to 6-membered heterocyclic, or R4 is an optionally substituted 9- or 10-membered bicyclic heterocyclic, having at least one heteroatom selected from oxygen, sulfur or nitrogen; R5 is a 5- or 6-membered heterocyclic containing at least one nitrogen, optionally substituted by one or two groups selected from oxo or fused bicyclic 9 or 10 membered heterocyclic having at least one heteroatom selected from oxygen, sulfur or nitrogen; R6 and R7 are independently hydrogen, C1- alkyl or phenyl, which is optionally substituted by one or two C-i4 alkyl groups; Ra and Rg are independently hydrogen, phenyl (which may be substituted by 1 or 2 C- alkyl groups), or Rs and Rg are independently C -4 alkyl, which is optionally substituted by 1 or 2 groups selected from: phenyl, C 1-4 alkoxy, cyano, 5-membered heteroaryl containing 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, or the 6-membered heteroaryl group containing from 1 to 3 nitrogen atoms, hydroxy, oxo, carboxy; And it is an atom of oxygen or sulfur; n is 0 or an integer from 1 to 3; m is 0, 1 or 2; and pharmaceutically acceptable salts and solvates thereof. Another embodiment of the invention provides compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, wherein: R is (CH2) NA-X-R4; A is a group selected from -N (R5) -, -N (R5) C (0) -, - N (R5) S (0) 2-, or -N (R5) C (Y) N (R6) -; Ri is hydrogen, C1_6alkyl or C3alkenyl; R2 is hydrogen or a hydroxyl protecting group; R3 is hydrogen or halogen; X is substituted C-MO alkylene chain optionally interrupted by a bivalent radical group selected from -O-, -N (R5) -, -C (O) -, -N (R5) C (Y) N (R6) -, -S (0) m-, -N (R5) C (0) -, - C (0) N (R5) -, -N (R5) C (0) C (0) -, -C (0) 0- or -C (NOR7) - or X is optionally substituted C2 alkenylene chain or optionally substituted C2-io alkynylene chain, wherein said C2-10 alkenylene or C2-10 alkynylene chains are optionally interrupted by a bivalent radical selected from -O-, -N (Rs) -, - C (0) -, -N (R5) C (Y) N (R6) -, -S (0) m-, -N (R5) C (0) -, -C (0) N (R5) - , -N (R5) C (0) C (0) -, -C (0) 0- or -C (NOR7) -; R4 is selected from: hydrogen, optionally substituted phenylene, optionally substituted C3-7 cycloalkyl, optionally substituted 9 to 10 membered aromatic bicyclic carbocyclic ring, optionally substituted 5 or 6 membered heteroaryl, wherein the 5-membered heteroaryl contains at least one heteroatom selected from oxygen, sulfur or nitrogen, and the 6-membered heteroaryl group contains 1 to 3 nitrogen atoms, 5 to 6 membered heterocyclic optionally substituted, or R 4 are optionally substituted bicyclic fused heteroaryl groups containing 9 or 10 ring members having at least one heteroatom selected from oxygen, sulfur or nitrogen; R5 and R6 are independently hydrogen, phenyl (which may be substituted by one or two C1-4 alkyl groups) or a nitrogen protecting group, or R5 and R6 are independently C- | 4 alkyl, which is substituted optionally by one or two groups selected from: phenyl, C 1-4 alkoxy, C 1-4 alkyl, cyano, nitro, 5-membered heteroaryl containing 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, and the heteroaryl group of 6 members contain from 1 to 3 nitrogen atoms; hydroxy, oxo, carboxy; R7 is hydrogen, Ci-4 alkyl or phenyl; And it is an atom of oxygen or sulfur; n is 0 or an integer from 1 to 5; and m is 0, 1 or 2. Another embodiment of the invention provides compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, wherein: R is hydrogen, cyano or (CH2) nA (CH2) mR4; Ri is C 1-6 alkyl or C 3-6 alkenyl, R 2 is hydrogen or a hydroxyl protecting group; R3 is hydrogen or halogen; R is selected from: hydrogen; optionally substituted phenyl; 9 to 10 membered aromatic fused bicyclic carbocyclic ring optionally substituted; 5 or 6 membered heteroaryl optionally substituted, wherein the 5-membered heteroaryl contains at least one heteroatom selected from oxygen, sulfur or nitrogen, and the 6-membered heteroaryl group contains from 1 to 3 nitrogen atoms; or R are optionally substituted bicyclic fused heteroaryl groups containing 9 or 10 ring members having at least one heteroatom selected from oxygen, sulfur or nitrogen; A is a bond or a selected group of N (Rs), N [C (0) Rs], N (R5) C (0), N (R5) S (02), N (R5) C (0) 0 , N = C (R6) or N (R5) C (X) N (R6); R5 and R6 are independently hydrogen, phenyl or C-1-alkyl 4; X is an oxygen or sulfur atom; n or m are independently 0, or an integer from 1 to 5, with the proviso that the sum of n and m is 0 or an integer from 1 to 5; and pharmaceutically acceptable salts and solvates thereof. Suitable pharmaceutically acceptable salts of the compounds of general formula (I) include acid addition salts formed with pharmaceutically acceptable organic or inorganic acids, for example, hydrochlorides, hydrobromides, sulfates, alkyl- or arylsulfonates (e.g., methanesulfonates or p-toluenesulfonates) ), phosphates, acetates, citrates, succinates, tartrates, fumarates and maleates. The compound of formula (I) and salts thereof can form solvates, and the invention includes said solvates. The solvates can be, for example, hydrates. In the following, references to a compound according to the invention include compounds of formula (I) and their pharmaceutically acceptable acid addition salts, together with pharmaceutically acceptable solvates. In the general formula (I) illustrated, the dark wedge-shaped link indicates that the bond is above the plane of the paper. The interrupted link indicates that the link is below the plane of the paper. Those skilled in the art will appreciate that the compounds of formula (I), wherein R is not hydrogen, contain at least one chiral center (i.e., the carbon atom shown as 21 in formula (I), and this is it can be represented by the formulas (1 a) and (1 b) The configuration for the carbon atom shown as 21 in the formula 1a, is referred to hereinafter as the configuration β and in the formula 1b as the configuration 21 a.

It will be understood that the two diastereomers (1a, 1), and mixtures thereof, are encompassed within the scope of the present invention. The compounds wherein R 2 represents a hydroxyl protecting group are, in general, intermediates for the preparation of other compounds of formula (I). When the OR2 group is a protected hydroxyl group, this is a non-toxic protecting group, conveniently OR2, or an acyloxy group (ie, acetoxy or benzyloxy). The term C 1-4 alkyl, as used herein as a group or part of the group, refers to a straight or branched alkyl group containing from 1 to 4 carbon atoms; examples of such groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl. The term "C-O alkyiene chain" refers to a straight or branched chain containing from 1 to 10 carbon atoms, and examples of such a group include, but are not limited to, methylene, ethylene, propylene, isopropylene, n-butylene , Sobutylene, tert-butylene, pentylene, n-heptylene, n-octylene, n-nonylene and n-decylene. The term "C2-10 alkenylene chain" refers to a straight or branched alkylene chain containing from 2 to 12 carbon atoms, and having at least one double bond; examples of such groups include ethylene, 2-propenylene, 1-propenylene, isopropenylene, 2-butenylene, 2-pentenylene, 2-hexenylene, and the like. The term "C2-10 alkynylene chain" refers to a straight or branched alkylene chain containing from 2 to 12 carbon atoms, and having at least one triple bond; examples of such groups include ethynylene, 2-propynylene, 1-propynylene, isopropynylene, 2-butynylene, 2-pentynylene, 2-hexenylene, and the like. The term "halogen" refers to a fluorine, chlorine, bromine or iodine atom. When R4 is a 5- or 6-membered heteroaryl group according to the invention, this includes furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, pyrazolyl, isoxazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,3. -oxadiazolyl, 2,3-thiadiazolyl, 1,4-triazolium, 1,4-oxadiazolyl, 1,4-thiadiazolyl, 1, 2,5-oxadiazolyl, 1, 2,5-thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,4-oxadiazolyl, 1, 2,5-triazinyl or 1, 3,5-triazinyl, and the like. The term "fused bicyclic heterocyclic group" of 9 to 10 members, refers to a bicyclic ring system 5,6 / 6,5 or 6,6, which contains at least one heteroatom selected from oxygen, sulfur or nitrogen, which may be saturated, unsaturated or aromatic. The term bicyclic fused heterocyclic group of 9 to 10 members also refers to a phenyl fused to a 5- or 6-membered heterocyclic group. Examples of such groups include benzofuranyl, benzothiophenyl, indolyl, benzoxazolyl, 3 H -imidazo [4,5-c] p'n'din-yl, dihydroftazinium, 1 H-imidazo [4,5-c] pyridin-1-yle. , imidazo [4,5-b] pyridyl !, 1,3 benzo [1,3] dioxolyl, 2H-chromanyl, isochromanyl, 5-oxo-2,3-dihydro-5H- [1,3] thiazolo [3, 2-a] pyrimidyl, 1,3-benzothiazolyl, 1, 4,5,6-tetrahydropyridazyl, 1, 2,3,4,7,8-hexahydropteridinyl, 2-thioxo-2,3,6,9-tetrahydro-1H-purin -8-yl, 3,7-dihydro-1 H-purin-8-yl, 3,4-dihydropyrimidin-1-yl, 2,3-dihydro-1,4-benzodioxinyl, benzo [1,3] dioxolyl, 2H -chromenyl, chromanyl, 3,4-dihydroftalazinyl, 2,3-dihydro-1 H-indolyl, 1,3-dihydro-2H-isoindol-2-yl, 2,4,7-trioxo-1, 2,3,4 , 7,8-hexahydropyridinyl, thieno [3,2-d] pyrimidinyl, 4-oxo-4,7-dihydro-3H-pyrrolo [2,3-d] pyrimidinyl, 1,3 dimetyl- 6-oxo-2-thioxo-2,3,6,9-tetrahydro-1 H-purinyl, 1,2-dihydroisoquinolinyl, 2-oxo-1,3-benzoxazoli, 2,3-dihydro-5H-1, 3- thiazolo [3,2-a] pyrimidinyl, 5,6,7,8-tetrahydro-quinazolinyl, 4-oxochromanyl, 3- benzothiazolyl, benzimidazolyl, benzotriazolyl, purinyl, furilpiridilo, tiofenilpirimidilo, tiofeniípiridilo, pirrolilpiridilo, oxazolilpiridilo, tiazolilpiridilo, 3,4 dihydropyrimidin-1-yl imidazolilpiridilo, quinoliilo, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pyrazolyl [3.4] pyridine, 1, 2 di hydroisoquinolinyl, cinolinyl, 2,3-dihydro-benzo [1,4] dioxin-6-yl, 4,5,6,7-tetrahydro-benzo [b] thiophenyl-2-yl, 1,8-naphthyridinyl, 1,6-naphthyridinyl, 3,4-dihydro-2H-1,4-benzothiazine, 4,8-Dihydroxy-quinolinyl, 1-oxo-1,2-dihydro-5-quinolinolinyl or 4-phenyl- [1, 2,3] thiadiazolyl, and the like.

The term 5- or 6-membered heterocyclic group refers to a 5- or 6-membered ring member containing at least one heteroatom selected from oxygen, sulfur or nitrogen, which may be saturated or unsaturated. Examples of such groups include piperidyl, 2-oxodihydrofuranyl, piperazinyl, morpholinyl, pyrazolidinyl, 1,2-dihydro-3H-pyrazolyl, imidazolidinyl or pyrrolidinyl, and the like. The term "fused bicyclic carbocyclic group" of 9 to 10 members, refers to a bicyclic carbocyclic ring system 5,6 / 6,5 or 6,6, which can be saturated, unsaturated or aromatic. It also refers to a phenyl fused to a saturated or unsaturated carbocyclic group of 5 or 6 members. Examples of such groups include naphthyl, 1, 2, 3, 4 tetrahydronaphthyl, n-nyl or indanyl, and the like. The term optionally substituted phenyl, optionally substituted 5 to 6 membered heterocyclic group, optionally substituted 9 to 10 membered fused bicyclic carbocyclic group, optionally substituted 9 to 10 membered fused bicyclic heterocyclic group, or optionally substituted 5 or 6 membered heteroaryl group , refers to a 5- to 6-membered heterocyclic, a fused bicyclic carbocyclic of 9 to 10 members, a bicyclic 9 to 10 membered fused heterocyclic, or a 5- or 6-membered heteroaryl, as defined above, which is substituted by 1 to 4 groups, which may be the same or different, selected from group (CH2) pRio, where p is zero or an integer from 1 to 4, and Rio is selected from: halogen, C1-4 alkoxy, alkyl C1-4, hydroxy, cyano, nitro, oxo, trifluoromethyl, carboxy, NR8R9, C0R8, CONRgRg, NHCORg, NHS02R8, S (0) qR6 (where q is 0 or an integer from 1 to 2), phenyl (substituted optionally e by halogen, C1-4 alkoxy or NR8R9); phenoxy; 5-membered heteroaryl containing at least one heteroatom selected from oxygen, sulfur or nitrogen, and a 6-membered heteroaryl group containing at least one nitrogen atom, which 5- or 6-membered heteroaryl can be substituted by Ci-alkyl -4 or cyano; or fused bicyclic heterocyclic of 9 or 10 members. When R 4 is an optionally substituted C 3-7 cycloalkyl, said group is optionally substituted by 1 or 2 substituents, which may be the same or different, and selected from C 1-4 alkyl, halogen, cyano, nitro, trifluoromethyl and NR 6 R 7. When X is an alkylene chain of CMO, a C2-io alkynylene chain or a C2-io alkenylene chain, which is interrupted by a bivalent radical selected from -O-, -NR8-, -C ( O) -, -N (R8) C (Y) N (Rg) -, -S (0) m-, -N (R8) C (0) -, -C (0) N (R8) -, N (R8) C (0) C (0) -, -C (0) 0- or -C (NORg) -, refers, for example, to C-10-O- alkylene, Ci-io- alkylene NR8C (Y) NR9-, C, 10-NR8 alkylene, C1-10-C (O) - alkylene, C1-10-S (O) m- alkylene, C1-10-NRsC (O) - alkylene, alkylene of C1 10-C (O) NR8-, alkylene of C ^ - ^ C ^ CtO) -, alkylene of C1 10-C (O) O-, alkylene of C110C (NOR6), alkenylene of C2 10-O -, alkenylene of C2 10-NR8-, alkenylene of C2 _10-C (O) -, alkenylene of C2 10-NR8C (Y) NRg-, alkenylene of C2 10-S (O) m-, alkenylene of C2 10- NR3C (O) -, alkenylene of C2 10-C (O) NRs-, alkenylene of C2.10-N (R8) C (O) C (O) -, alkenylene of C2 10-C (0) 0-, alkenylene of C2 10-C (NOR6), alkynylene of C2 10-O-, alkynylene of C2 10-NR8-, alkynylene of C2 10-C (O) -, alkynylene of C2_10 -NR8C (Y) NR9-, C2-10-S (O) m- alkynylene, C2-10-NRsC (O) - alkynylene, C2-10-C (O) NR8- alkynylene, C2-10-N alkynylene ( Rg) C (O) C (O) -, C2.10-C (O) O- alkynylene, C2_10-C alkynylene (NORe), or refers to an alkylene chain of C1-10, a chain of C2-io alkenylene or a C2-10 alkynylene chain containing a divalent radical group selected from: -O-, -NRg-, -C (O) -, -NR8C (Y) NRg-, -S (0 ) m-, -NR8C (0) - or - C (0) NR8-. When A is -N (Rg) -, -N (R6) S (0) 2- or -N (R6) C (Y) N (R7), and when X is a substituted C-O alkylene optionally interrupted by a bivalent radical selected from -O-, -N (R8) -, -N (R8) C (Y) N (Rg) -, -S (0) m- , -N (R8) C (0) - or -N (R8) C (0) C (0) -, said bivalent radicals are preferably linked to group A by means of an optionally substituted alkylene chain containing at least two carbon atoms. When A is -N (R6) -, -N (R6) S (0) 2- or -N (R5) C (Y) N (R7), and when X is an optionally substituted C2-io alkenylene chain or an optionally substituted C2-io alkynylene chain, and when these chains are interrupted by a bivalent radical selected from -O-, -N (R8) -, -N ( R8) C (Y) N (Rg) -, -S (0) m-, -N (R8) C (0) - or -N (R8) C (0) C (0) -, said bivalent radicals are they preferably bind to group A by means of an optionally substituted alkenylene or alkynylene chain containing at least 4 carbon atoms and having -CH 2 - as terminal groups. A preferred group of compounds of formula (I) are those wherein the carbon atom shown as 21 is in the β-configuration.

R is preferably (CH2) nA-X-R4 or (CH2) nR5. Ri is preferably methyl or 2-propenyl. R2 is preferably hydrogen. R3 is preferably hydrogen or fluorine. When R 4 is a 5- or 6-membered heteroaryl group, it is preferably midazolyl, pyrazolyl, thiophenyl, 1,2,3-triazolyl, pyridinyl or furanyl. When R 4 or R 5 is a 5- or 6-membered heterocyclic group, it is preferably imidazolidinyl or pyrrolidinyl. When R is a fused bicyclic 9 or 10 membered heteroaryl group, it is preferably quinolinyl, quinoxalinyl, indolyl, purinyl, 1,3-benzo [1,3] dioxolyl, benzothiazolyl, 1 H-benzimidazol-1, 3-benzoxazoyl , 1 H-pyrrolo [2,3-b] pyridinyl, 1,3-dihydro-2H-isoindolyl, 3 H -imidazo [4,5-c] pyridin-3-yl, 3 H -imidazo [4,5-b] pyridin-3-yl, 7H-purin-7-yl, 1 H-imidazo [4,5-c] pyridin-1-yl or 4,5,6,7-tetrahydro-benzo [b] thiophen-2-yl . R5 is preferably 1-pyrrolidinyl, which is optionally substituted by an oxo or benzo [1, 3] dioxollium. X is preferably an Ci-5 alkylene chain, a C2-5 alkenylene chain or a C2-5 alkynylene chain, wherein said chains are: i) optionally interrupted by a bivalent radical group selected from -O -, -N (R8) -, -C (O) -, -N (R8) C (Y) N (R9) -, -S (0) m-, -N (R8) C (0) -, -C (0) N (R8) -, -N (R8) C (0) C (0) -, -C (Q) 0- or -C (NOR6) -, and / or ii) optionally substituted by one or two groups selected from: CM alkyl, oxo, C1-4 alkoxy, halogen, cyano, phenoxy, hydroxy, NR8R9, N (R8) C (0) Rgl = NOR6, NR8C (Y) NR9 > 0 phenyl optionally substituted, and n is preferably 0 or 1. Preferred compounds of the invention are those wherein A is selected from -NH "-NHC (O) - or -NHC (Y) NH-. where n is 0 or 1, they are particularly preferred.A preferred class of compounds of formula (I) is that wherein X is a C1-4 alkylene chain, which is optionally interrupted by a bivalent radical selected from -O -, -NH-, -C (O) -, -NHC (O) -, -S (0) 2- -S-, and / or said alkylene chain of Ci-4 is optionally substituted by a group selected from NH 2, C 4 alkyl, oxo or -N-OH A particularly preferred group of compounds of formula (I) is that wherein R 4 is phenyl (optionally substituted by 1 to 3 groups which may be the same or different selected from nitro, amino, methyl, C1-4 alkoxy (ie, methoxy or hydroxy), 1-imidazolyl (optionally substituted by 1 to 3 groups which may be the same or different selected from pyridin-2-yl, pyridin-3-yl) , p iridin-4-yl, phenyl, m-nitrophenyl, dichlorophenyl, C 1-4 alkyl (i.e., methyl, trifluoromethylphenyl, thiophen-2-yl, thiazol-2-yl), 3-trifluoromethylpyrazol-4-yl, 1 - pyrazolyl (optionally substituted by 1 to 3 groups which may be identical or different from halogen (i.e., chloro, fluoro), pyridin-2-ylo, pyridin-4-l, quinolin-2-yl, quinolin-4 -yl, quinoxalin-2-yl, pyrimidin-4-yl, Ci-4 alkyl (i.e., methyl, 1,3-benzooxazol-2-yl, p-chloro phenyl, difluoro phenyl, pyrazin-2-yl thiazole -5-yl, 1 H-indol-3-yl, 1 H-indol-2-yl, 3-methoxy-quinoxaIin-2-yl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 4-pyridinyl, -pyridinyl (optionally substituted by an amino), 5-methyl-furan-2-yl, 3-thiophenyl, 6-methoxy-7H-purin-7-yl, quinoxalin-2-yl, 3-methoxy-quinoxalin-2-yl, 6-methoxy-2-oxo1, 3-benzoxazol-3 (2H) -yl, 1 H -pyrrolo [2,3-b] pyridin-1-yl, 2- (methylthio) -1 H -benzimidazole- 1-yl, 1,3-dioxo-1,3-dihydro-2H-iso-undol-2-yl, 6-methoxy-2-oxo-1,3-benzoxazo! -3 (2H) -yl, 3H- imidazo [4,5-b] pyridin-3-yl, 1,3-benzoxazol-2-yl, benzothiazol-2-yl, 1,3-benzo [1,3] dioxolyl, 3- (5-cyano-3, 4-dimethylin-2-yl) -1 H-1, 2,4-triazol-1-yl, 2,3-dihydro-benzo [1,4] dioxin-6-yl, 2,4-dimethyl-, 3 -thiazol-5-yl or 4-oxo-4,5,6,7-tetrahydro-benzo [b] thiophen-2-yl. A particularly preferred group of compounds of formula (I), is where Ri is methyl, R2 or R3 is hydrogen, A is -NH-, -NHC (O) -, X is alkylene chain of CM, which is optionally interrupted by a bivalent radical selected from -O-, -NH-, -C (O) -, -NHC (O) -, -S (0) 2- -S- and / or said C -4 alkylene chain is optionally substituted by a selected group of NH2, Ci-, oxo or N-OH alkyl, R4 is a group selected from 4- (pyridin-3-yl) -imidazol-1-yl, 4- (pyridin-3-yl) -imidazole-1- ilo, quinoxalin-2-yl, quinoxalin-2-yl, quinolin-4-yl, quinoxalin-2-yl, - (2,3-dihydro-benzo [, 4] dioxin-6-yl, 4-oxo- 4,5,6,7-tetrahydro-benzo [b] thiophen-2-yl, 4-methoxy-3-nitro-phenyl, 2-hydroxy-4,5-dimethoxy-phenyl, 3-hydroxy-4-methoxy- phenyl, 3,4-dimethoxy-phenyl, 4-hydroxy-3-methoxy-phenyl, 3-methoxy-quinoxalin-2-yl, 3- amino-4-methoxy-phenyl, 4- (pyridin-3-yl) -imidazol-1-yl, quinolin-4-yl, 4-pyrimidin-4-yl-pyrazol-1-yl, 2- (methylthio) ) -1 H-benzimidazol-1-yl, - [3- (4-chlorophenyl) -1 H -pyrazol-5-yl] propylamino) -methylene], 6-methoxy-2-oxo-1,3-benzoxazole- 3 (2H) -yl, 1 H-pyrrolo [2,3-b] pyridin-1-yl, 3- (2,4-dimethyl-1,3-thiazol-5-yl) -1 H-pyrazole! 1-ilo, 4- phenyl-1 H-imidazol-1-yl, 4-pyridin-4-yl-1 H-imidazol-1-yl, thiophen-2-yl, 3- (5-cyano-3,4-dimethyl) lthien-2-yl) -1 H-1, 2,4-triazol-1-yl, quinolin-3-yl, 1,3-thiazol-2-yl, and n is 0 or 1. Particularly preferred compounds of the invention are selected from: (11 S, 21 R) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12, 11 - [oxycarbonyl- (4- ( 4- (pyridin-3-yl) -imidazol-1-yl) -butyramidomethyl) -methylene] -erythromycin A; (11S, 21R) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxocarbonyl- (3- (4- (pyridin-3-yl) -imidazol-1-yl) -propionamidomethy1) -methylene] -erythromycin A; (11S, 21R) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) -acetamidomethyl) - methylene] -erythromycin A; (11 S.21 R) -3-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (3- (quinoxalin-2-ylsulfanyl) -propionamidomethyl) -methylene ] -erythromycin A; (11S, 21R) -3-methylene-1-l, 12-dideoxy-6-0-methyl-3-oxo-12,1-l- [oxycarbonyl - [(quinolin-4-ylmethyl) - amino] -methyl) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxocarbonyl- (3- (quinolin-4- L) -propionamido) -methylene] -erythromycin A; (1 1 S, 21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) -acetamido) -rneti! ene] -erithromycin A; (11 S, 21 R, S) -3-decladinosyl-1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl - ((4- (2,3-dih) Dro-benzo [1,4] dyoxy-6-yl) -4-oxo) -butramide) -methylene-erythromycin A; (11S, 21R, S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (4- (4-oxo-4,5 , 6,7-tetrahydro-benzo [b] thiophen-2-yl) -4-oxo-butyramido) -methylene] -erythromycin A; (1 1 S.21 R, S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (4- (4-methoxy-3-nitro phenyl) -4-oxo-butyramido) -methylene] -erythromycin A; (HS ^ I SJ-S-decladinosyl-I L ^ -dideoxy-eO-methyl-S-oxo-12,1 - [oxycarbonyl- (4- (2-hydroxy-4,5-dimethoxy-phenyl) -4- oxo-butyramido) -methylene] -erythromycin A; (1 1 S, 21 R, S) -3-declanedosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (4- (3-hydroxy-4-methoxy-phenyl) -4-oxo-butyramido) -methylene] -erythromycin A; (11S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1 - [oxycarbonyl- (4- (3,4-dimethoxy-phenyl) -4-oxo-butyramido) -methylene] -erythromycin A; (11S, 21R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methy [-3-oxo-12,11- [oxycarbonyl- (4- (4-hydroxy-3-methoxy phenyl) -4-oxo-butyramido) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (2- (3-methoxy-quinoxalin-2- ilsulfanyl) -acetamido) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (2- (quinoxalin-2-yloxy) - acetamido) -methylene] -erythromycin A; (1 1 S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (4- (3-amino-4- methoxy-pheny [(4-oxo-butyramido) -methylene] -erythromycin A; (11 S, 21 R, S) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-2,1- [oxycarbonyl- (4-hydroximino-4- (4-methoxy) 3-nitro-phenyl) -butyramido) -methylene] -erythromycin A; (11 S, 21 R, S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (2- (quinoxalin-2-sulfonyl) -acetamide ) -methylene] -erythromycin A; (1 1 S.21 R, S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (3- (4- (pyridine-3- il) -imidazol-1-yl) -propylamino) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (2- (4- (pyridine -3-yl) -imidazol-1-yl) -ethylamino) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosi! -1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxocarbonyl- (4- (quinolin-4-! l) -butyllamino) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1 - [oxycarbonyl- (2- (quinolin-4-yl) - ethylamino) -methylene] -erythromidin A; (11S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (3- (4-pyrimidin-4-yl) -pyrazol-1-yl) -propylamino) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1 - [oxycarbonyl- (3- [2- (methyl) ) -1 H-benzimidazol-1 -yl] propylamino) -methylene] -erythromycin A; (11S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11 - [oxycarbonyl- (3- [3- (4-chlorophenyl) -1 H-pyrazol-5-yl] propylamino) -methylene] -erythromycin A; (11 S, 21 R, S) -3-decladinosyl-1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1 - [oxycarbonyl- (3- (6-methoxy-2-oxo -1, 3-benzoxazol-3 (2H) -yl) propylamino) -methylenej-erythromycin A; (11 S.21 R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (3- (1 H -pyrrolo [2, 3-b] pyridin-1-yl) propylamino) -methyl ene] -eritrorriycin A; (HS.ZI RS a-decladinosyl-H. ^ - dideoxy-eO-meityl-S-oxo- ^ I-Ioxycarbonyl-iS-IS ^^ - dimethyl-l ^ iazol-Si-I H -pyrazol-li propylamino ) -methylene] -erythromycin A; (11 S, 21 R, S) -3-dec! Adinosl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (3- (quinoxalin-2 -ylsulfanyl) -propylamino) -methylene] -erythromycin A; (11S, 21R, S) -3-methsid-1-l, 12-dideoxy-6-0-methyl-3-oxo-12 1- [oxycarboni 3- (4-phenn-1 H-i'midazole-1 -yl) propyl) amino) -mei! -leno] -erythromycin A; (HS ^ I RS ^ S-Decladinosyl-H. ^ - dideoxy-eO-methyl-S-oxo-12 1- [oxocarbonyl- (2- (4-pyridin-4-yl-1 H-imidazole -1-yl) ethylamine) -methylene] -erythromycin A; (11S, 21 R, S) -3-decidynosyl-1 1, 12-d-deoxy-6-0-methyl-3- oxo-12,1 1- [oxocarbonyl- (2- (quinoxalin-2-ylsulfanii) -ethylamino) -methylene] -ertromethin A; (11 S, 21 S) -3-decladinosyl-1 1 , 12-dideoxy-6-0-methyl-3-oxo-2,11- [oxocarbonyl- (3- (4- (thiophen-2-yl) -midazol-1-yl) -propylamino) -methylene ] -erithromycin A; (11S, 21R, S) -3-decladinosl-1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- ( (3- [3- (5-cyano-3,4-dimethylthien-2-yl) -1 H-1, 2,4-triazol-1-yl] propyl) amino) -methyl-ene] -eritrom A (11 S, 21 R, S) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,1- [[oxycarbon] - ((3 -quinolin-3-ylpropyl) amino) -methylene] -erythromycin A; (11 S.21 R, S) -3-decladinosyl-1 1.12-dideoxy-6-0-metH-3-oxo-12,11- [oxycarbonyl - ((3- [4- (3-nitrophenyl) -1 H-imidazol-1-yl] propyl) amino) -methylene] -erythromycin A; (11S, 21R, S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12 1- [oxycarbonyl - ((2- [3- (1,3-thiazole- 2-i1) -1 H-pyrazol-1-yl] ethyl) amino) -methyl erythromycin A; (IIS ^ I RS ^ decladinosil-l lia-dideoxy-BO-methyl-S-oxo-12, 1 1 - [oxycarbonyl - ((2- (4-phenyl-1 H-imidazo! -1-yl) ethyl) amino) -methylene] -erythromycin A; (11 S, 21 R, S) -3-decladinosyl-1 1, 12-dideoxy-2-fluoro-6-0-methyl-3-oxo- 2,11- [oxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) -acetamido) -methylene] -erythromycin A; and (HS ^ I RS ^ S-decladinosyl-l ^^ - dideoxy ^ -fluoro-eO-methyl-S-oxo -12,11- [oxocarboni! - (3- (4- (pyridin-3-yl) -imidazol-1-yl) -propylamino) -methylene] -erythromycin A. Other preferred compounds of the invention include: (11S.21 S) -3-decladinosyl-1 1, 12-dideoxy-6-O-methyl-3-oxo-12,11- [oxycarbonyl- (2- (4- (pyridin-3-yl) - imidazol-1-yl) -ethylamino) -methylene] -erythromycin A; (1 1S, 21 S) -3-decladinosyl-1 1, 12-dideoxy-6-O-methyl-3-oxo-12, 1- [oxycarbonyl- (2- (quinolin-4-yl) -ethylamino) -metholene] -ertromethine A; (11 S.21 S) -3-declaidinosyl-1 1, 12-dideoxy-6-O- methyl-3-oxo-12,1 1- [oxycarbonyl- (3- (4- (pyridin-3-yl) -imidazol-1-yl) -propylamino) -methylene] -erythromycin A; (11 S.21 S) -3-declanedi-1-l, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (2- (quinoxalin-2-lysulfanyl) - acetamido) -methylene] -enthromycin A; (1 1 S, 21 S) -3-declaidinosyl- 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxocarbonyl - ((4- (2,3-dihydro- benzo [1,4] dyoxy-6-yl) -4-oxo) -butyramido) -methylene] -erythromycin A; (1 1 S, 21 S) -3-dec! Adinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 - [oxycarbonyl- (4- (4-methoxy-3-nitro- phenyl) -4-oxo-butyramido) -metholene] -erithromycin A; (1 1 S.21 S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (4- (2-hydroxyl) -4,5-diiTethoxy-phenyl) -4-oxo-butyramido) -metholene] -erythromycin A; (11 S, 21 S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11 - [oxycarbonyl- (4- (4-oxo-4,5,6, 7-tetrahydro-benzo [bthiophen-2-yl) -4-oxo-butyramido) -methylene] -erithromycin A; (1 1 S.21 S) -3-decladinosyl-1 1, 12-d-deoxy-6-0-methyl-3-oxo-12,1 - [oxycarbonyl- (3- (4-quinoline- 2-yl-H-pyrazol-1-yl) propylamino) -methyl-ene] -erythromycin A; (1 1 S, 21 S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methylene-3-oxo-12,1 - [oxycarbonyl- (4- (3 ^ -d) methoxy-phenyl) -4-oxo-butyramido) -methylene] -ertromicin A; (1 1 S, 21 S) -3-decidinosil- 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxocarbonyl- (4- (4-hydroxy-3-methoxy) Phenyl) -4-oxo-butyramide) -metholene] -entromycin A; and (11 S, 21 S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (3- (4- (thiophen-2-yl) -imidazol-1-yl) -propylamino) -methylene] -eritrom A. The compounds according to the invention also exhibit a broad spectrum of antibacterial activity against a wide range of clinical pathogenic microorganisms. For example, by using a stepwise dilution test in standard microtiter broth, it has been found that the compounds of the invention exhibit useful levels of activity against a wide range of pathogenic microorganisms including Stapfty / ococcus aureus, Sfreptococcus pneumon / ae. , Moraxe // a catarrña / ís, Streptococcus pyogenes and Haemopñí / us / nf / uenzae. In addition, the compounds of the invention are also active against intracellular pathogens such as the species C / amydia pneumomae, Cfi / amycf / a spp, Leg / onef / a pneumophiYa or Mycop / asthma pneumoniae. The compounds of the invention can therefore be used for the treatment of various diseases caused by pathogenic bacteria in humans and animals. Thus, in accordance with another aspect of the present invention, a compound of formula (I), or a physiologically acceptable salt thereof, is provided for use in therapy in a human or animal subject. According to another aspect of the invention, there is provided the use of a compound of formula (I) or a physiologically acceptable salt thereof, in the manufacture of a therapeutic agent for the treatment of systemic or topical bacterial infections in the body of a human or animal In accordance with another aspect of the invention, there is provided a method for treating the body of a human or non-human animal to combat bacterial infections, which method comprises administering to the body an effective amount of a compound of formula (I), or a physiologically acceptable salt thereof. The term "treatment" also means that it includes prophylaxis. When it is possible that, for use in therapy, a compound of the invention can be administered as the chemical raw material, it is preferred to present the active ingredient as a pharmaceutical formulation. The compounds of the invention can be formulated for administration in any convenient form for use in human or veterinary medicine, and the invention therefore includes within its scope, pharmaceutical compositions comprising a compound of the invention adapted for use in medicine. human or veterinary Said compositions may be presented for use in conventional manner with the aid of one or more suitable vehicles or excipients. Compositions of the invention include those in a form specially formulated for parenteral, oral, buccal, rectal, topical, implant, ophthalmic, nasal or genitourinary use.

The compounds according to the invention can be formulated for use in human or veterinary medicine by injection (eg, by intravenous bolus injection or infusion, or by intramuscular, subcutaneous or intrathecal routes), and can be presented in a dose form unit, in ampoules, or other unit dose containers, or in multiple dose containers, if necessary, with an added preservative. The compositions for injection may be in the form of suspensions, solutions or emulsions, in oily or aqueous vehicles, and may contain formulatory agents such as suspending, stabilizing, solubilizing and / or dispersing agents. Alternatively, the active ingredient may be in the form of a sterile powder for reconstitution with a suitable vehicle, eg, sterile, pyrogen-free water, before use. The compounds of the invention can also be presented for human or veterinary use in a form suitable for oral or buccal administration, for example, in the form of solutions, gels, syrups, mouthwashes or suspensions, or a dry powder for reconstitution with water or another suitable vehicle before use, optionally with flavoring and coloring agents. Solid compositions such as tablets, dragees, capsules, pills, pills, boluses, powders, pastes, granules, bales or premixed preparations can also be used. Solid and liquid compositions for oral use can be prepared according to methods well known in the art. Said compositions may also contain one or more pharmaceutically acceptable carriers and excipients, which may be in solid or liquid form. The compounds of the invention can also be administered orally in veterinary medicine, in the form of a liquid concoction such as a solution, suspension or dispersion of the active ingredient, together with a pharmaceutically acceptable carrier or excipient. The compounds of the invention can also be formulated, for example, as suppositories, for example, containing conventional suppository bases for use in human or veterinary medicine, or as pests, for example, containing conventional weighing bases. The compounds according to the invention can be formulated for topical administration, for example, in human and veterinary medicine, in the form of ointments, creams, gels, lotions, shampoos, powders (including sprayable powders), loons, buffers, sprays, dips , aerosols, drops (for example, eye, ear or nose drops) or washes. Aerosol sprays are conveniently supplied from pressurized packages, with the use of a suitable propellant, for example, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane, carbon dioxide, or other suitable gas. For topical administration by inhalation, the compounds according to the invention can be supplied for use in human or veterinary medicine, by means of a nebulizer. Pharmaceutical compositions for topical administration may also contain other active ingredients such as corticosteroids or antifungals, as appropriate. The compositions may contain 0.01-99% of the active material. For topical administration, for example, the composition will generally contain 0.01-10%, more preferably 0.01-1% of the active material. For systemic administration, the daily dose used for treatment of adult humans will vary from 2-100 mg / kg of body weight, preferably 5-60 mg / kg of body weight, which can be administered in 1 to 4 daily doses , for example, depending on the route of administration and the condition of the patient. When the composition comprises dose of dosage, each unit will preferably contain from 200 mg to 1 g of active ingredient. The duration of the treatment will be determined by the speed of response, rather than by an arbitrary number of days. The compounds of general formula (I), and salts thereof, can be prepared by the general method described below. In the following description, the groups ,, R2, R3, R4, R5, R6, R7jR8, Rg, R10, n, m, p, q, X, Y and A, have the meaning defined by the compounds of formula ( I), unless otherwise indicated. The compounds of formula (I), wherein A is -N (R6) C (0) - or -N (R6) S (02) -, can be prepared by reaction of compounds of formula (II): wherein Rn is a cladinose derivative of formula (III), wherein R2a is a hydroxy, or hydroxy, protecting group, R12 is hydrogen, or R12 together with Rp is an oxygen atom, with a suitable activated derivative of the acid ( IV), HOC (0) XR4 (IV), or with an appropriate activated sulfonic acid derivative (V) HOS (0) 2XR4 (V) respectively and, if required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group into the 3-oxo; c) removal of the protective group R2. Suitable activated derivatives of the carboxyl group or the sulfonic acid include the acyl halide, mixed anhydride or corresponding activated ester, such as a thioester or a pentafluoroester. The reaction is preferably carried out in a suitable aprotic solvent, such as halohydrocarbon (for example dichloromethane) or α, β-dimethylformamide optionally in the presence of a tertiary base such as pyridine, dimethylaminopyridine or triethylamine, and at a temperature within the scale from 0o to 120 ° C.

Compounds of formula (I), wherein A is -N (R6) C (Y) N (R7) - and R7 is optionally substituted phenyl or Cw alkyl, can be prepared from compounds of formula (II), where Rn and R12 have the meaning defined above, by reaction with a compound of formula R4XNR C (Y) L (VI), wherein L is a suitable leaving group as defined above, and R7 is phenyl or alkyl of d- 4, if required, by subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group into the 3-oxo and c) removal of the protective group R2. Compounds of formula (II), wherein A is -N (R6) C (Y) NH-, can be prepared from compounds of formula (II), wherein Rp and Ri2 have the meaning defined above, by reaction with compounds of formula R4XN = C = Y (VII), if required, by subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxyl group to the 3-oxo and c) removal of the protective group R2. Compounds of formula (I), wherein A is -N (R6) -, can be prepared from compounds of formula (II), wherein Rp and R 2 have the meaning defined above, by reaction with compounds of formula R4XL (VIII), where L is a suitable leaving group. If required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxyl group into the 3-oxo and c) removal of the protective group R2. Suitable leaving groups for this reaction include halogen (for example, chlorine, bromine or iodine) or sulfonyl (for example, tosyl or methanesulfonyl). Compounds of formula (I), wherein A is a group N (R6) C (0) 0, wherein R6 is hydrogen, phenyl or C1-4 alkyl, can be prepared from compounds of formula (II), wherein R and R-12 have the meaning defined above, by reaction with the appropriate haloformate compound of the formula R 4 XOC (0) l (IX), wherein L is a suitable leaving group ta! as halogen (e.g., chlorine or bromine) and, if required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group into the 3-oxo and c) removal of the protective group R2. The reactions of compounds (II) with compounds (VI), (VII), (VIII) or (IX), are conveniently carried out in a solvent such as tetrahydrofuran, acetonitrile or halohydrocarbon (for example, dichloromethane), optionally in the presence of a base such as triethylamine, and at a temperature within the range of 0 to 80 ° C. Compounds of formula (I), wherein A is a group N = C (R6), can be prepared from compounds of formula (II), wherein Rn is hydroxy, R12 is hydrogen, or Rn together with R12 is a oxygen atom, by reaction with a compound of formula R4XCHO (X) and, if required, subjecting the resulting compound to one or more of the following operations a) conversion of the 3-hydroxy group to the 3-oxo and b) removal of the protective group R2. The reaction is preferably carried out in a solvent such as a haiohydrocarbon, for example dichloromethane, at a temperature within the range of 0 to 50 ° C. Compounds of formula (I), wherein A is N [C (0) R6], can be prepared by treating a compound of formula (XI), wherein Rn and R 2 have the defined meaning for compounds of formula (II), by acylation reaction with the activated carboxylic acid of formula (Xla) R6COOH (Xla).

(XI) and, if required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group to the 3-oxo- and c) removal of the protective group R2. The reaction is preferably carried out in the presence of a base such as a tertiary amine, for example, triethylamine or pyridine, in a solvent such as a haiohydrocarbon, for example dichloromethane, at a temperature within the range from 0 ° to 50 ° C. ° C. Suitable activated derivatives of the carboxyl group or the sulfonic acid include the acyl halide, mixed anhydride or corresponding activated ester, such as a thioester or a pentafluoroester. Compounds of formula (I), wherein R is hydrogen, can be prepared by decarboxylation of a compound of formula (XII), wherein Rp and R 2 have the defined meaning for the compounds of formula (II) followed, if required , of subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group into the 3-oxo and c) removal of the protective group (XII) The decarboxylation can be carried out in the presence of a lithium salt such as lithium chloride, preferably in an organic solvent such as dimethyl sulfoxide. Compounds of formula (I), wherein R is cyano, can be prepared by cyclization of chlorine derivatives (XIII), wherein Rn and R 2 have the defined meaning for the compounds of formula (II), (XIII) with potassium cyanide, and conveniently, in the presence of a solvent such as?,? - dimethylformamide and, if required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group into the 3-oxo and c) removal of the protective group R2. In a preferred embodiment of the invention, compounds of formula (I), wherein A is -N (R6) - and X is C2-io alkylene interrupted by NR8-, -N (R8) C (Y) N (R9) ) -, -N (R8) C (0) - or -N (R8) C (0) C (0) -, can be prepared by reaction of a compound of formula (XIV), wherein Xa is C2-io-N (R8) alkyl, and R12 are defined as in formula (II), with compounds LXbR4 (XV), wherein L is a suitable leaving group, Xb is a group selected from C (Y) N (Rg), C (Y) N (Rg) C 1-8 alkylene, C (O), C (0) alkylene of Ci-8, C (0) C (0) or C (0) C1-8 alkylene and, if required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxy group into the 3-oxo and c) removal of the protective group R2. Compounds of formula (XIV) can be prepared from compounds of formula (II), by reductive N-alkylation with a compound of formula HC (0) C2-9 alkyl N (R6) (XVI). The reaction is conveniently carried out in a protic solvent such as alcohol, ie, methanol, and in the presence of a suitable metal reducing agent, such as sodium borohydride or sodium triacetoxyborohydride. Compounds of formula (I), wherein n is 2 or 3, and wherein X is optionally substituted and / or C1-10 alkylene optionally substituted, can be prepared from a phosphite of formula (XVII), wherein R and R 12 have the meaning defined in formula (II), and R 13 is C 1-4 alkyl, (XVII) (XVIII) by reaction of Wittig-Horner with an aldehyde of formula (XVIII), followed by reduction of the corresponding double bond, using hydrogen and a metal catalyst (e.g., palladium) and, if required, subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III); b) conversion of the 3-hydroxyl group into the 3-oxo and c) removal of the protective group R2. The Wittig-Horner reaction is carried out in the presence of a suitable organic or inorganic base, such as 1,8-diazabicyclo [5.4.0] undec-7-ene or diisopropylethylamine, in an aprotic solvent such as dichloromethane, preferably at a temperature ranging from -20 ° to + 80 ° C. In the reactions described above, the cladinose derivatives of formula (III) can be removed by treatment with an organic or inorganic acid. An example of a suitable inorganic acid is hydrochloride. The reaction is carried out in the presence of water or an organic solvent such as tetrahydrofuran, dichloromethane, or mixtures thereof. In the reactions described above, the conversion of the 3-hydroxy group to the 3-oxo can be carried out by oxidation reaction using a modified Moffatt-Pfitzner method. A suitable oxidizing agent includes N, N-dimethylaminopropyl-3-ethyl carbodiimide-dimethyl sulfoxide. The reaction is suitably carried out in the presence of pyridinium trifluoroacetate in a chlorinated solvent such as methylene chloride at -10 ° C to 25 ° C. In another embodiment, the oxidation can be carried out using Dess Martin periodonyl reagent. Compounds of formula (I), wherein A is NR6, and wherein R6 is optionally substituted Ci-4 alkyl, can be prepared by treating amino groups of formula (II), wherein R6 is hydrogen, with an alkylating agent L -R6 (XIX), where L is a suitable leaving group, in the presence of a base. Compounds of formula (II), wherein n is 0, can be prepared by intramolecular Michael reaction of compounds of formula (XX), wherein R-i4 is a suitable nitrogen protecting group, and Rii and R-12 have the meaning defined in formula (II), in the presence of an organic base such as 1,8-diazabicyclo [5.4.0] undec-7-ene.

(XX) The reaction is conveniently carried out in a polar aprotic solvent such as acetonitrile, dimethylformamide, or an aqueous mixture thereof, followed by removal of the nitrogen protecting group R-4. The suitable nitrogen protecting group R1 for use in this reaction includes diarylmethylidene, such as diphenylmethylidene. Compounds of formula (II), wherein n is 1, can be prepared by reduction of a compound of formula (XXI), wherein Rn and R12 have the meaning defined in formula (II).

The reduction can be carried out using conventional reducing agents known in the art, to convert a nitrile group to an amino group. In this way, for example, the reaction can be carried out using hydrogen in the presence of Raney nickel as a catalyst. The reaction is preferably carried out in an alcohol solvent such as methyl, ethyl or isopropyl alcohol. Compounds of formula (XXI) can be prepared by cyclization of chlorine derivatives (XXII), wherein Rn and R12 have the defined meaning for the compounds of formula (II), (XXII) with potassium cyanide and, conveniently, in the presence of a solvent such as?,? - dimethylformamide followed, if required, by subjecting the resulting compound to one or more of the following operations a) hydrolysis of the cladinose derivative (III) ); b) conversion of the 3-hydroxy group into the 3-oxo and c) removal of the protective group l¾. Compounds of formula (XVII) can be prepared by heating a compound of formula (XX11I): (XXIII) in an aprotic solvent such as?,? - dimethylformamide, at a temperature ranging from 60 ° to 120 ° C, in the presence of a base such as 1,8-diazabicyclo [5.4.0] undec-7 -one Compounds of formula (XXIII) can be prepared by reaction of chlorine derivatives of formula (XXII) with (R130) 3 phosphite. The reaction is carried out in a suitable aprotic solvent such as a hydrocarbon (i.e., toluene or xylene), α, β-dimethylformamide, or by heat at a temperature within the range of 80 ° to 160 ° C. Compounds of formula (XXII) can be prepared by reacting the corresponding hydroxy derivatives (XXIV), (xxi) wherein Rn and R12 have the meaning defined in formula (II), with a suitable activated derivative of HOCOCH2CI acid (XXV). Thus, for example, the esterification can be carried out by reaction with anhydride (CICH2CO) (XXVI) in a suitable aprotic solvent such as a halohydrocarbon (for example, dichloromethane) or?,? - dimethylformamide, and in the presence of a tertiary base such as pyridine, dimethylaminopyridine or triethylamine, and at a temperature within the range of 0 ° C to 120 ° C.

Compounds of formula (XX) can be prepared by treating a compound of formula (XXII) with sodium azide, subjecting the resulting azido compound to the following operations: a) reduction by conventional means, reducing the azido group to amino group, and b) conversion to the group NH2 in the nitrogen protecting group N = R- | 4, wherein R- | 4 has the meaning defined above and, if required, by removal of the hydroxy protecting group R2. The reduction to amino group can be carried out, for example, in the presence of triphenylphosphine and water. In another embodiment of the invention, compounds of formula (XX) can be prepared by treating a compound of formula (XXII) with NH OH in the presence of solvent; a suitable solvent for this reaction is dimethylsulfoxide and water. Compounds of formula (XXIV) can be prepared by reacting derivatives of 11, 12-carbonate erythromycin A (XXVII), in which case R-11 and R12 have the meaning defined in formula (II), with a strong base such as 1 , 8-diazabicyclo [5.4.0] undec-7-ene.

(XXVII) The elimination reaction can be carried out in an organic solvent such as toluene, ethyl acetate,?,? - dimethylformamide, or a mixture thereof, conveniently with heating. Compounds of formula (XXVII) can be prepared from erythromycin A derivatives of formula (XXVI11), (XXVIII) by conversion of the 2'-hydroxy group to the corresponding hydroxy protected group, and by conversion of the 11, 12 hydroxy to a carbonate group, using triphosgene in a suitable solvent such as dichloromethane, in the presence of pyridine. Compounds of formula (XXVIII) can be prepared by alkylation of an oxime of formula (XXIX): (XXIX) wherein R-15 is an oxime protecting group, and R2 and 1a are a hydroxyl protecting group, with a compound of formula L-R1 (XXX), wherein L is a suitable leaving group such as a halogen (for example, chlorine, bromine or iodine) or a suifonil (for example, tosyl, methanesulfonyl), in the presence of a base, followed by hydrolysis of the cladinose derivative and conversion of the 3-hydroxy group to the 3-oxo. The reaction with the compound (XXX) is preferably carried out in a solvent such as a halohydrocarbon (for example, dichloromethane), an ether (for example, tetrahydrofuran, dimethoxyethane), acetonitrile, and the like. Examples of bases that may be used include potassium hydroxide, cesium hydroxide, tetraalkylammonium hydroxide, sodium hydride, potassium hydride, and the like, followed by subsequent removal of the oxime protecting group. A suitable oxime protecting group is R15, for example, 1-isopropoxycyclohex-1-yl. Oxime compounds (XXIX) can be prepared by reaction of a compound of formula (XXXI), wherein R2 and R a are hydrogen, using methods analogous to those described in USP 6110965.

(XXXI) Compounds of formula (I), wherein R 3 is halogen, can be prepared from compounds of formula (I), wherein R 3 is hydrogen, and R 2 is hydroxy protecting group, by reaction with a halogenating agent in the presence of an organic or inorganic base. Suitable halogenating agents include N-fluoro-benzenesulfonimide, SELECTFLUOR ™ for fluorination, pyridinium tribromide or cyanogen bromide for bromination, or hexachloroethane for chlorination. A convenient base for the reaction is selected from sodium hydride, potassium hydride, sodium carbonate, potassium hexamethyldisilazide, lithium diisopropylamine or pyridine. The reaction is carried out in a solvent such as N, N-dimethylformamide, tetrahydrofuran or N-methylpyrrolidone, or a mixture thereof, conveniently at a temperature within the range of -78 ° to 60 ° C. Alternatively, the halo group in the 2-position of the ring of the macrolide can be introduced in a previous step of the synthesis of the compounds of formula (I) .Thus, for example, it can be introduced by treating a compound of the formulas (II), (IX), (XII), (XV), (XVI), (XVII), (XVIII), (XIX), (XXII) or (XXIII), provided that Rn together with Ri2 are an atom of oxygen, using the method described above to obtain compound (I), wherein R 3 is a halo group Compounds of formula (I), wherein R is (CH 2) n R 5, can be prepared by intramolecular cyclization of a compound of formula (XXXII), (XXXII) wherein L is a suitable leaving group, such as halogen (i.e., chlorine or bromine), X is C4.5 alkylene chain, optionally substituted by one or two groups selected from 9 or 10 membered fused bicyclic heterocyclic oxo has at least one heteroatom selected from oxygen, sulfur or nitrogen. The reaction is carried out suitably in the presence of an inorganic base or an organic base. Alternatively, compounds of formula (I), wherein R is (0? 2)? (?), Can be prepared by intramolecular reductive N-aicylation of a compound of formula (XXXIII): (XXXIII) wherein R 6 are fused 9- or 10-membered heterocyclic groups, and r is 3 or 4. This reaction was conveniently carried out in an aprotic solvent such as dichloroethane, and in the presence of a suitable metal reducing agent, such as borohydride. sodium or triacetoxyborohydride sodium. The compounds of formulas (IV), (V), (VI), (VII), (VIII), (IX), (X), (Xla), (XIII), (XVI), (XVIII), (XIX), (XXI) or ( XXV) are known, or are commercially available compounds, or can be prepared using methods known in the art. The nitrogen protection reaction can be carried out with a suitable imine such as benzophenone imine, in an aprotic solvent, for example dichloromethane, preferably at room temperature. When it is desired to isolate a compound of formula (I), or a salt thereof, for example, a pharmaceutically acceptable salt, this can be achieved by reacting the compound of formula (I), in the form of the free base, with an amount of suitable acid and in a suitable solvent such as an alcohol (e.g., ethanol or methanol), an ester (e.g., ethyl acetate) or an ether (e.g., diethyl ether or tetrahydrofuran). Pharmaceutically acceptable salts can also be prepared from other salts, including other pharmaceutically acceptable salts of the compound of formula (I), using conventional methods. Suitable hydroxy protective reagents are those described by T. W. Greene and P. G. M Wuts in Protective Groups in Organic Synthesis 2a. ed., John Wiley &; Sons, Inc. 1991, citation incorporated herein by reference. Examples of suitable hydroxy protecting reagents include acetic anhydride, benzoic anhydride or a trialkylsilyl chloride in a protic solvent. Examples of the aprotic solvent are dichloromethane, N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, and the like. The hydroxyl protecting groups can be removed by standard well-known procedures. For example, when R2a is a trialkylsilyl group, it can be removed by treatment with tetrabutylammonium fluoride and acetic acid, or by reaction with a source of fluoride ions such as triethylamine tris (hydrogen fluoride), or this process is carried out conveniently in a solvent such as tetrahydrofuran or acetonitrile. When R2 or R2a is alkanoyl (ie, acetyl or benzoyl), these can be removed by treatment with an alcohol (e.g., methanol or ethanol). In any of the formulas (I), (II), (XI), (XIV), (XVII), (XXI), (XXXII) or (XXXIII) shown above, when there is an asymmetric carbon atom and it is not shown specific configuration, then the formula includes all possible configurations. Specific stereoisomers of the compounds of formula (I) as defined in formula 1a and 1b, essentially free of the other stereoisomers, can be prepared using the general procedures described above, starting with the appropriate stereoisomer of formula (II). The process described above for preparing the compounds of formula (II) will generally give a mixture of diastereoisomers. The individual stereoisomers of the compounds of formula (II) can be separated from each other by conventional techniques such as fractional crystallization, or more particularly by column chromatography using, for example, a silica column. In a preferred embodiment of the invention, the individual stereoisomer of formula (1 a), wherein R is NH 2, can be prepared by epimerization reaction of a compound of formula (1 b) or a mixture of (a) and (b) ), where R is NH2. The reaction is carried out in the presence of benzaldehyde and DBU, followed by hydrolysis of the mine derivative with inorganic acid such as hydrochloride. The reaction is carried out suitably in an aprotic solvent such as, for example, toluene or N, N-dimethylformamide. The assignment of the R or S configuration in position 21, has been made according to the rules of Cahn, Ingold and Prelog, Experientia 195 6, 12, 81. When examples are obtained as a diastereoisomeric mixture of 21 R and 21 S , unless otherwise specified, the 1 H-NMR spectra refer to the 1 H-NMR spectra of the predominant diastereomer (i.e., 21 S). In the intermediates and examples, unless otherwise indicated: The proton magnetic resonance spectra (1H-NMR), were recorded at 500 MHz, the chemical changes are reported in ppm downfield (d) of Me4Si, used as an internal standard, and they are assigned as singles (s), doublets (d), doublets of doublets (dd), triplets (t), quartets (q) or multiple bands (m). The mass spectra were acquired with a 1100 MSD system from Hewlett Packard equipped with a binary pump (Agilent Technologies), operating in positive electrospray ionization mode. The LC / MS data (liquid chromatography / mass spectroscopy) were obtained using an HP 1 100 LC system (Agilent Technologies) equipped with a Sedex Model 75 evaporative light scattering detector (Sedere), coupled with a mass spectrometer Platform LCZ (Micromass), operating in positive electrospray ionization mode.

The chromatographic analysis conditions were: Waters Xterra MS C18 column (4.6 x 30 mm, 2.5 μ ??); flow rate of 0.8 ml / min; mobile phase: aqueous solution of NH4OAc (10 mM, pH 6.8) (A) and acetonitrile (B). The purifications by LC (liquid chromatography) were carried out with a Waters 600 semipreparative system equipped with a binary pumping system and a Jasco UV light detector. The chromatographic analysis conditions were: Supelcosil ABZ + Plus column (10 cm x 21.2 mm, 5 μ ??); flow rate of 8 ml / min; mobile phase: aqueous solution of NH4Oac (10 mM, pH 6.8) (A) and acetonitrile (B). Column chromatography was carried out on silica gel 60 (230-400 mesh, ASTM-Merck AG Darmstaadt, Germany). TLC (thin layer chromatography) monitoring was carried out using 60 F254 from Merck as a TLC plate. The phase separations were carried out using a microfiltration-filtration tube, with polypropylene support (Whatman). The resin washes were carried out in Extract-clean tube (Altech). The purifications of the raw products were carried out using SCX cartridges (Varian). PS-Trisamine resin (based on polystyrene) (Argonaut Technologies Inc.) was used to remove excess reagents. The abbreviations that have been used in the description of the following synthesis methods are: brine for saturated aqueous solution of sodium chloride, DBU for 1,8-diazabicyclo [5.4.0] undec-7-ene, DCE for 1, 2 -dichloroethane, DCM for dichloromethane, DIPEA for N, N-düsopropylethylamine, DMAP for 4-dimethylaminopindin, DMF for N, N-dimethylformamide, DMSO for dimethyl sulfoxide, EDC for 1- (3-dimethylaminopropyl) -3 hydrochloride -ethylcarbodiimide, Et20 for diethyl ether, EtOAc for ethyl acetate, HATU for 0- (7-azabenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, HOBT for hydrated 1-hydroxybenzotriazole, iPrOH for 2-propanol, MeOH for methanol, MTBE for methyl tert-butyl ether, TEA for triethylamine, and THF for tetrahydrofuran.

INTERMEDIARY 1 2'-0-Acetyl-11 2-carbonate-3-decladinosyl-11,12-d-deoxy-6-Q-methyl-3-oxo-erythromycin A To a solution of 2'-0-acetyl-3-decladinosyl-6-0-methyl-3-oxo-erythromycin A (0.500 g) in anhydrous DCM (20 mL) under a nitrogen atmosphere, sequentially pyridine (1.5 mL) was added. ) and phosgene (20% sol in toluene, 1 mL). The reaction mixture was stirred overnight at room temperature, and then quenched with a saturated aqueous solution of NaHCO3 (50 mL). The organic phase was washed with water (50 mL), dried over a2SO4, concentrated under reduced pressure, and the crude product was purified by flash chromatography (eluting with: DCMWleOH 90 \ 10), to give the title compound (0.360 g). TLC: DCMWleOH 90 \ 10 (Rf = 0.6).

INTERMEDIARY 2 2'-0-Acetyl-3-declaidinosyl-11-deoxy-10,11 -didehydro-6-Q-methyl-3-oxo-erythromycin A To a solution of intermediate 1 (0.210 g) in a 2 \ 1 mixture of EtOAc-toluene (6 mL) was added DBU (0.05 mL), and the mixture was heated at 85 ° C for 6 hours. The reaction mixture was allowed to reach room temperature, the solvent was evaporated, and the crude product was purified by flash chromatography (eluting with: DCMWleOH 90 \ 10), to give the title compound (0.150 g). TLC: DCMWleOH 90 \ 10 (Rf = 0.7).

INTERMEDIARY 3 2'-Q-Acetyl-12-chloroethanoyl-3-declaidinosyl-11-deoxy-10.11 -didehydro-6-Q-methyl-3-oxo-erythromycin A To a solution of intermediate 2 (0.150 g) in anhydrous DCM (3 mL) cooled to 0 ° C, pyridine (0.05 mL), chloroacetic anhydride (0.065 g) and DMAP (5 mg) were added sequentially under nitrogen atmosphere. The reaction mixture was stirred for 4 hours, then quenched with water (10 mL) and extracted with DCM (2x10 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 80 \ 20), to give the title compound (0.060 g). TLC: DCMWleOH 90? 10 (Rf = 0.8).

INTERMEDIARY 4 (11 S21 / a-2'-0-Acetyl-3-declaidinos-11,13-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (iminomethyl) -methylene -erythromycin A To a solution of Example 1 (0.137 g) in iPrOH (20 mL), Raney nickel (0.100 g) was added. The reaction mixture was saturated with hydrogen (5 atmospheres) and stirred at room temperature for 24 hours. After removing e! Catalyst by filtration and evaporating the solvent under reduced pressure, the crude material was purified by flash chromatography (eluting with: DCMWleOH 95V5), to give the title compound (0.012 g). 1 H-NMR (CDC) d: 7.61, 7.07 (t + t, 1 H), 4.94, 4.82 (dd + dd, 1 H), 4.76 (m, 1 H), 4.39, 4.38 (d + d, 1 H), 4.24, 4.22 (d + d, 1 H), 3.83 (q, 1 H), 3.55 (m, 1 H), 3.26 (m, 1 H), 3.13 (m, 1 H), 3.02, 2.90 (d + d, 1 H), 2.96 (m, 1 H), 2.70 (m, 1 H), 2.65, 2.64 (s + s, 3 H), 2.60, 2.50 (m + m, 1 H), 2.26 (s, 6 H), 2.07, 2.06 (s + s, 3 H), 1.94 (m, 1 H), 1.77-1.64 (m, 2H), 1.55 (m, 1 H), 1.50, 1.46 (s + s, 3 H), 1.33 (d + d, 6 H), 1.32 (s, 3 H), 1.21 (d, 3 H), 1.17 (m, 1 H), 1.14 (s, 3 H), 0.97, 0.96 (d + d, 6 H), 0.83, 0.80 (t + t, 3 H). TLC: DCMWleOH 95 \ 5 (Rf = 0.65).

INTERMEDIARY ß roxícarbonil-fiminometiD-methyleneol-erythromycin A A solution of intermediate 4 (0.010 g) in MeOH (1 ml_) was stirred for 48 hours, and then concentrated under reduced pressure, to give the title compound (0.009 g). 1 H-NMR (CDCl 3) d: 7.61, 7.09 (t + t, 1 H), 4.94, 4.83 (dd + dd, 1 H), 4.86 (bm, 1 H), 4.32, 4.30 (d + d, 1 H), 4.26, 4.24 (d + d, 1 H), 3.86 (m, 1 H), 3.56 (m, 1H), 3.13-3.10, 2.96 (m, 3 H) 3.02 (m, 1 H), 2.88 (bs, 1 H), 2.66 (s, 3 H), 2.50 (m, 1 H), 2.30 (s, 6 H), 1.95 (m, 1 H), 1.85, 1.76 (m, 1 H), 1.70 -1.60 (m, 2H), 1.55 (m, 1H), 1.49, 1.46 (s + s, 3 H), 1.4-1.3 (m, 6 H), 1.30-1.14 (m, 2H), 1.0-0.9 ( d, 3 H), 0.84, 0.81 (t + t, 3 H). TLC: DC \ MeOH 95 \ 5 (Rf = 0.45).

INTERMEDIARY 6 2 ', 4"-0-Diacetyl-6-O-methyl-erithromycin A To a solution of 6-O-methyl-erythromycin A (50 g) in anhydrous DCM (240 mL), TEA (26.1 mL), DMAP (0.392 g) and acetic anhydride (15.2) were added at 0 ° C under nitrogen atmosphere. mL). The resulting mixture was stirred at 0 ° C for 45 minutes, and overnight at room temperature. The mixture was then diluted with saturated aqueous NH 4 Cl solution (240 mL), and extracted with DCM (2x200 mL). The aqueous phase was neutralized with saturated aqueous NaHCO 3 solution, and extracted again with DCM (2 × 200 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to give the title compound (50.7 g). m \ z ([MH] +) = 832.

INTERMEDIARY 7 1112-Carbonate-2 \ 4 '' - 0-diacetyl-11,12-d-deoxy-6-0-methyl-erythromycin A To a solution of intermediate 6 (200 g) in anhydrous DCM (1600 mL) cooled to 0 ° C, pyridine (117 mL) and a solution of triphosgene (71.2 g) in anhydrous DCM (400 mL) were added under nitrogen. . The resulting mixture was stirred at 0 ° C for 30 minutes, and then at room temperature for 15 hours. The mixture was then diluted with water (750 mL), and extracted with DCM (2x500 mL). The organic layer was washed with water (3x300 mL), dried over Na2SO4 and concentrated under reduced pressure to give the title compound (200 g). m \ z ([MHf) = 858.

INTERMEDIARY 8 11-Deoxy-2 ', 4"-Q-d-acetyl-10,11 -didehydro-6-O-methyl-erythromycin A To a solution of intermediate 7 (50.5 g) in a 2 \ 1 mixture of toluene \ EtOAc (675 mL), DBU (12 mL) was added at room temperature. The resulting mixture was stirred at 85 ° C for 8 hours, and at room temperature for 5 hours. The reaction mixture was then diluted with brine (250 mL), extracted with EtOAc (2x350 mL), and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the crude material was purified by crystallization (from acetone \ water), to give the title compound (46 9) -m? ([MH] +) = 814.

INTERMEDIARY 9 12-Chloroethanoyl-11-deoxy-2 ', 4"-Q-diacetyl-0.11 -d! Dehydro-6-O-methyl-erythromycin A To a solution of intermediate 8 (20 g) in anhydrous DC (340 mL), cooled to 0 ° C, pyridine (6 mL) and cycloacetic anhydride (8.4 g) were added under a nitrogen atmosphere, and the reaction was allowed to reach the room temperature. After 16 hours, the reaction mixture was washed with water (300 mL), and then saturated aqueous solution of NH 4 Cl (150 mL) and brine (150 mL) were extracted with DCM (2x300 mL). The organic phase was dried over Na 2 SO and concentrated under reduced pressure. The crude material was dissolved in acetone (50 mL) and water (100 mL) was added under vigorous stirring. The precipitate was filtered and dried in vacuo to give the title compound (20.4 g). m \ z ([MH] +) = 890.

INTERMEDIARY 10 2'-O-Acetyl-12-chloroethanoyl-3-declaidinosyl-11-deoxy-10,11-didehydro-6-Q-methyl-e ritrom i ci na A To a solution of intermediate 9 (20.2 g) in THF (200 mL) cooled to 0 ° C, an aqueous solution of 3N HCl (400 mL) was added dropwise. The reaction mixture was allowed to reach room temperature, and stirred overnight. The solution was neutralized with saturated aqueous solution of NaHCC > 3, and extracted with DCM (2x200 mL). The organic layer was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by rapid filtration over silica gel (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (15.4 g). m \ z ([MHf) = 690.

INTERMEDIARY 11 (11 £ 21 / a- -O-Acetyl-S-declaidinosiM 1, 12-dideoxy-6-Q-methylene-12,1-roxycarbonyl- (cyano) -rnetylene-1-erythromycin A To a solution of intermediate 10 (0.400 g) in anhydrous DMF (30 mL), potassium cyanide (0.380 g) was added under a nitrogen atmosphere. The mixture was stirred at room temperature for 2 hours, quenched with saturated aqueous NaHCO3 solution (50 mL), and extracted with DCM (70 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound (0.430 g). TLC: DCM \ MeOH 90 \ 10 (Rf = 0.50).

INTERMEDIARY 12 (11 ^ l / a-a'-O-AcetH-S-declaidinosyl-ll. ^ - dideoxy-eO-methyl-l-1-l-oxycarbonyl- (iminomethyl) -methylene-1-erythromycin A § INTERMEDIARY 13 (11 £ 21yq-2'-0-Acetyl-3-decladinosyl-11,12-dideoxy-6-Q-methyl-12.11- [oxycarbonyl- (aminomethyl) -metholene-erythromycin A To a solution of intermediate 11 (0.100 g) in PrOH (10 ml_), Raney nickel (0.100 g) was added. The mixture was saturated with hydrogen (5 atmospheres), and stirred at room temperature for 24 hours. After removing the catalyst by filtration and evaporating the solvent, the crude product was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound 12 (0.038 g) and the compound. of title 13 (0.027 g). TLC: DCMUvleOH 90 \ 10, Rf (intermediate 12) = 0.43. TLC: DCMWleOH 90 \ 10, Rf (intermediate 13) = 0.2.

INTERMEDIARY 14 (11, 21 > q-2'-0-Acetit-3-decladinosyl-11, 12-dideoxy-6-Q-methyl-12.11-roxycarbonyl- (chloroacetamidomethyl) -methylene | -erythromycin A To a solution of intermediate 13 (0.054 g) in anhydrous DCM (2 mL), pyridine (0.010 mL), chloroacetic anhydride (0.016 g) and DMAP (catalytic amount) were added sequentially under nitrogen atmosphere. The mixture was stirred at 0 ° C for 1 hour. The reaction was quenched with saturated aqueous NaHCO3 solution (5 mL), and extracted with DCM (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 98 \ 2), to give the title compound (0.036 g). TLC: DCMWleOH 90 \ 10 (Rf = 0.43).

INTERMEDIARI0 15 (11 £ 21 / a- -O-Acetyl-S-declaidinosyl-l 1,2-dideoxy-6-Q-methyl-12,11-roxycarbonyl- (chlorobutylamidomethyl) -methylene] -erythromycin A To a solution of intermediate 13 (0.100 g) in anhydrous DCM (4 mL), pyridine (0.024 mL), 4-chlorobutyryl chloride (0.016 mL) and DMAP (catalytic amount) were added sequentially under nitrogen atmosphere. The mixture was stirred at 0DC for 2 hours. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL), and extracted with DCM (20 mL).

The organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (0.100 g). TLC: DCM \ MeOH 90 \ 10 (Rf = 0.40). m \ z ([H] +) = 789.

INTERMEDIARY 16 2'-Q-Acetyl-12-aminoethanoyl-3-declaidinosM 1 -deoxy-10,11 -didehydro-6 -? - methyl-erythromycin A To a solution of intermediate 10 (3 g) in DMSO (40 mL), a solution of 32% aqueous ammonia (8 mL) was added dropwise over 10 minutes at room temperature. The reaction mixture was stirred for 2 hours at 50 ° C. After cooling to 0 ° C, water (40 mL) was added, and the mixture was extracted with MTBE (2x45 mL). The collected organic layers were washed with brine (40 mL), dried over Na 2 SO 4 and concentrated under reduced pressure to give the title compound (2.5 g). TLC: DCM WleOH 10 \ 1 (Rf = 0.28).

INTERMEDIARY 17 2'-0-Acetyl-12- (benzhydrylidene) -aminoethanyl-3-declaidinosyl-11-deoxy-10,11 -didehydro-6-O-methyl-erythromycin A A solution of intermediate 16 (4.0 g) and benzophenone imine (2.6 mL) in anhydrous DCM (40 mL) was stirred at room temperature under nitrogen atmosphere. After 36 hours, the reaction was quenched with water (100 mL) and extracted with DCM (3x300 mL). The organic layer was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (3.5 g). TLC: DCM \ MeOH 10 \ 1 (Rf = 0.38).

INTERMEDIARY 18 (11S21 ^) -2'-0-Acetyl-3-declaidinosyl-11,12-dideoxy-6-Q-methyl-12,11-foxycarbonyl- (benzhydrylidenoamino) -methylene-erythromycin A A solution of intermediate 17 (3.0 g) and DBU (0.540 mL) in acetonitrile (135 mL) and water (15 mL) was stirred at room temperature for 3 hours. After evaporating the solvent, the crude material was dissolved in DCM (300 mL) and washed with water (100 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (3.0 g).

TLC: DCM WleOH 10 \ 1 (Rf = 0.38).

INTERMEDIARY 19 11-Deoxy-2 \ 4"-O-diacetyl-10 1-didehydro-12-methoxycarbonyl-ethanoyl-6-O methyl-erythromycin A To a solution of intermediate 8 (0.500 g) in anhydrous toluene (100 mL) under nitrogen atmosphere, pyridine (0.250 mL) and methylmalonyl chloride (0.158 mL) were added at 0 ° C. The temperature was allowed to reach room temperature. After stirring for 1 hour, water (50 mL) was added, and the organic layer was washed with brine (50 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the crude material was purified by rapid filtration over silica gel, to give the title compound (0.560 g). m \ z ([MH] +) = 914.

INTERMEDIARY 20 2'-0-Acetyl-3-declaidinosyl-11-deoxy-10,11 -didehydro-12-methoxy-carbonylethanoyl-6-O-methyl-erythromycin A and INTERMEDIARY 21 2'-0-Acetyl-3 -decladinosyl- 1 -deoxy-10,11 -didehydro-12-carboxy-ethanoyl-6-O-methyl-erythromycin A A solution of intermediate 19 (0.500 g) in an aqueous solution of HCI at 2N (50 mL) and THF (1 mL) was stirred at room temperature for 6 hours. Then, the mixture was cooled to 0 ° C and a saturated aqueous solution of potassium carbonate was added until a pH = 9 was obtained. The mixture was extracted with DCM (2x50 mL), the organic phase was washed with brine (25 mL), dried over Na 2 SO, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH = 95 \ 5), to give the title compound 20 (0.180 g) and the title compound 21 (0.180 g). m \ z ([MH] +) (broker 20) = 714. m \ z ([MH] +) (broker 21) = 700.

INTERMEDIARY 22 12.11 -roxycarbonyl- (methoxycarbonyl) -methyleneol-erythromycin A A solution of intermediate 20 (0.150 g) and DBU (0.050 mL) in water (1.5 mL) and acetonitrile (13.5 mL) was stirred at 40 ° C for 6 hours. After evaporating the solvent under reduced pressure, the residue was dissolved in DCM (20 mL), the organic phase was washed with water (50 mL), dried over Na 2 SO, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (0.070 g). m \ z ([MHf) = 714.

INTERMEDIARY 23 (10 / ?, 5 *, 11 / a-2'-Q-Acetyl-3-decladinos8l-11, 12-dideoxy-6-Q-methyl-12,11-foxycarbonylmethylene-erythromycin A A mixture of intermediate 22 (0.050 g) and lithium chloride (0.006 g) in DMF (1 mL) was heated to reflux for 4 hours. The mixture was allowed to reach room temperature and poured into an aqueous 3% NaHCO 3 solution at 0 ° C, then extracted with DCM (2x15 mL). The organic phase was washed with water (2x10 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (DCMWIeOH: 95 \ 5), to give the compound of (0.010 g). m \ z ([MHf) = 656.

INTERMEDIARY 24 (11: 21) -2 ^ 0-AcetH-3-decladinosl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (chloro) -ethylamino ) -methylene1-erythromycin A To a solution of Example 7 (0.335 g) in anhydrous acetonitrile (3 mL), chloroacetaldehyde (50% by weight solution in water, 0.127 mL) was added under a nitrogen atmosphere, and the resulting mixture was stirred for 20 hours at room temperature. Sodium cyanoborohydride (1 M in THF, 0.500 mL) and acetic acid (0.041 mL) were added, and the reaction mixture was stirred for 6 hours at room temperature. After evaporating the solvent, the residue was dissolved in DCM (25 mL) and washed with an aqueous solution of 5% NaHCO 3 (10 mL). The organic phase was dried over Na 2 SO 4 and concentrated under reduced pressure to give the title compound (0.300 g). m \ z ([MH] +) = 731.

INTERMEDIARY 25 (11 £ 21 a-2'-Q-Acetyl-3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-12,11-roxycarbonH- (3-quinolinyl-carbonylamino ^ To a solution of intermediate 13 (0.028 g) in anhydrous DMF (2.5 mL), 3-quinolinecarboxylic acid (0.008 g), HATU (0.017 g) and DIPEA (0.017 mL) were added sequentially under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours, and then the solvent was evaporated under vacuum. The residue was dissolved in DCM (15 mL), and washed with water (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash chromatography to give the title compound (0.022 g). TLC: DCM \ MeOH 90 \ 10 (Rf = 0.37).

INTERMEDIARY 26 (11. £ 21 ¾-2'-Q-Acetyl-3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-12,11-roxycarbonyl- (4- (4- (pyridine-3- il) -imidazol-1-yl) -butyramidomethyl) -metH erythromycin A To a solution of intermediate 13 (0.050 g) in anhydrous DMF (5 mL), intermediate 49 (0.019 g), HATU (0.030 g) and DIPEA (0.031 mL) were added sequentially under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 hours, and then the solvent was removed under vacuum. The residue was dissolved in DCM (20 mL), the organic phase was washed with water (15 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash chromatography to give the title compound (0.042 g). TLC: DCMWleOH 90 \ 10 (Rf = 0.37).

INTERMEDIARY 27 (11 £ 21 / a-2'-Q-Acetyl-3-declaidinosyl-11, 12-dideoxy-6-0-methylene-12,11-roxycarbonyl ^ 3- (4- (pyridine-3- in-imidazol-1-yl) -propionamidomethymethylene-erythromycin A To a solution of intermediate 13 (0.050 g) in anhydrous DMF (5 mL), intermediate 48 (0.020 g), HATU (0.030 g) and DIPEA (0.031 mL) were added sequentially under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours, and then the solvent was removed under vacuum. The residue was dissolved in DCM (15 mL), the organic phase was washed with water (10 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by flash chromatography to give the title compound (0.042 g). TLC: DCM \ MeOH 90 \ 10 (Rf = 0.28).

INTERMEDIARY 28 (11 £ 21 a-2'-0-Acetyl-3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-12,11-foxycarbonyl-f2-f4-pyridine-3-pyridine; l) -imidazole-1-yl) acetamidomethyl) -methylene-1-erythromycin A To a solution of 3- (1 / imidazol-4-yl) -pyridine (0.005 g) in anhydrous DMF (2 mL) cooled to 0 ° C, sodium hydride (0.001 g) was added under a nitrogen atmosphere. The reaction mixture was stirred at 0 ° C for 1 hour, and then a solution of intermediate 14 (0.030 g) in anhydrous DMF (1 mL) was added. After 16 hours at room temperature, the reaction was quenched with water (5 mL), and the mixture was extracted with DCM (10 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by preparative TLC (eluting with: DCM \ MeOH 90 \ 10), to give the title compound (0.020 g). TLC: DCMMVIeOH 90 \ 10 (Rf = 0.35).

INTERMEDIARY 29 (1. £ 21> q-2'-0-Acetyl-3-declaidinosyl-1,2-dideoxy-6-Q-methyl-12,11- [oxycarbonyl- (1- (pyrrolidin-2-one) ) -rnetil) -methylene-1-erythromycin A To a solution of intermediate 15 (0.095 g) in anhydrous DMF (8 mL) cooled to 0 ° C, sodium hydride (0.004 g) was added under a nitrogen atmosphere. The mixture was stirred at 0 ° C for 1 hour, and at room temperature for 18 hours. Water (5 mL) was added, and extracted with a mixture of Et20 \ DCM 80? 20 (3x10 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound (0.050 g). m \ z ([MHf) = 753.

INTERMEDIARY 30 (11.S; 21 ^ -2 ^ 0-AcetM-3-decidnosyl-11 2-dideoxy-6-Q-methyl-12,11-roxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) - acetamidomethyl) -methyleneol-erythromycin A To a solution of intermediate 13 (0.075 g) in anhydrous DMF (7 mL), were added sequentially under nitrogen atmosphere acid (quinoxalin-2-ylsulfanyl) -acetic (0.029 g), HATU (0.046 g) and DIPEA (0.030 mL) ). The mixture was stirred at room temperature for 6 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (20 mL). The organic phase was washed with saturated aqueous NaHCO3 solution (2x15 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMW! EOH 90? 10), to give the title compound (0.069 g). m \ z ([MH] +) = 887.

INTERMEDIARY 31 (11 ^ 21 / ¾-2'-0-Acetyl-3-decladinosyl-11,12-dideoxy-6--0-methyl-12,11 - [oxocarbonyl- (3- (quinoxalin-2- iSulfanyl) -propionamidomethyl) -methylene1- erythromycin A To a solution of intermediate 13 (0.030 g) in anhydrous DF (3 mL), 3- (quinoxalin-2-ylsulfanyl) -propionic acid (0.012 g), HATU (0.018 g) and DIPEA were added sequentially under nitrogen atmosphere. 0.012 mL). The mixture was stirred at room temperature for 6 hours, and then the solvent was evaporated under reduced pressure. The residue was dissolved in DCM (15 mL), the organic phase was washed with saturated aqueous solution of NaHCO 3 (2x10 mL), dried over Na 2 SO 4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 90 \ 10), to give the title compound (0.035 g). m \ z ([MH] +) = 901.

INTERMEDIARY 32 (11 21 / a-2'-Q-Acetyl-3-decladinosil-11. 12-d-desoxl-6-Q-methyl-12,11-Foxicarbonyl-r (quinoline ^ -ylmethylene) -am A A solution of intermediate 13 (0.090 g) and quinoline-4-carbaldehyde (0.023 g) in anhydrous toluene (5 mL) was heated at 50 ° C for 8 hours under nitrogen atmosphere. Evaporation of the solvent under reduced pressure gave the title compound (0.100 g). m \ z ([MH] +) = 824.

INTERMEDIARY 33 2 ', 4"-0-D-acetyl-6-O-allyl-er> thromboxyme To a solution of 6-OAIil erythromycin A (1 g) in anhydrous DCM (5 mL) cooled to 0 ° C, TEA (0.5 mL), DMAP (0.008 g) and acetic anhydride (0.31 mL) were added under nitrogen atmosphere. . The resulting mixture was stirred at 0 ° C for 1 hour, and overnight at room temperature. Then, saturated aqueous NH 4 Cl solution (30 mL) was added, and the mixture was extracted with DCM (2x50 mL). The aqueous phase was neutralized with saturated aqueous solution of NaHCO 3, and extracted again with DCM (2x50 mL). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure to give the title compound (1 g). m \ z ([MH] +) = 858.

INTERMEDIARY 34 11 2-Carnate-2 4"-0-d ^ acetyl-11,12-dideoxy-6-0-allyl-er.} Thromycin To a solution of intermediate 33 (4.13 g) in anhydrous DCM (85 mL), pyridine (0.8 mL) and then phosgene (20% solution in toluene, 2.55 mL) were added at 0 ° C under nitrogen atmosphere. The resulting mixture was stirred at 0 ° C for 30 minutes, and then at room temperature for 1 hour. The reaction mixture was then diluted with water (150 mL), and extracted with DCM (2x200 mL). The organic layer was washed with water (3x100 mL), dried over Na2SO4 and evaporated under reduced pressure to give the title compound (4.02 g). m \ z ([MH] +) = 884.

INTERMEDIARY 35 11-Deoxi-2 ', 4"-O-diacetyl-10,11 -didehydro-6-O-allyl-erythromycin To a solution of intermediate 34 (4.02 g) in toluene (45 mL) and EtOAc (23 mL), DBU (0.71 mL) was added at room temperature. The resulting mixture was heated at 85 ° C for 6 hours. The mixture was then diluted with brine (100 mL), extracted with EtOAc (2x200 mL), and dried over Na2SO4. Evaporation of the solvent under reduced pressure and purification by flash chromatography of the crude material (eluting with: DCM \ MeOH \ NH4OH 95 \ 4 \ 0.01), gave the title compound (1.70 g). m \ z ([MH] +) = 840.

INTERMEDIARY 36 12-Chloroethanoyl-11-deoxy-2 ', 4"-Q-diacetyl-10,11 -didehydro-6-O-allyl-erythromycin A To a solution of intermediate 35 (1.7 g) in anhydrous DCM (50 mL) cooled to 0 ° C, pyridine (0.66 mL), DMAP (0.012 g) and chloroacetic anhydride (0.695 g) were added under nitrogen. The resulting mixture was stirred for 30 minutes at 0 ° C, and then at room temperature for 2.5 hours. The mixture was diluted with water (50 mL), neutralized with saturated aqueous NaHCO3 solution, and extracted with DCM (2x00 mL). The organic phase was washed with water (3x75 mL), dried over Na 2 SO 4 and evaporated under reduced pressure to give the title compound (1.8 g). m \ z ([MH] +) = 916.

INTERMEDIARY 37 2'-Q-Acetyl-12-chloroethanoyl-3-declaidinosyl-11-deoxy-10,11 -didehydro-6 -? - allyl-erythromycin A To a solution of intermediate 36 (1.8 g) in THF (35 mL), an aqueous solution of HCl at 6N (10 mL) was added at 0 ° C. The resulting mixture was stirred overnight at room temperature, and then diluted with water (50 mL). The pH of the solution was brought to 8-9 by the addition of solid NaHCO3 and aqueous 1% NaOH solution, and then the aqueous phase was extracted with DCM (2x100 mL). Evaporation of the solvent under reduced pressure and treatment of the residue with Et20 gave the title compound (1.4 g). m \ z ([MH] +) = 716.

INTERMEDIARY 38 (11 * 21 / ¾-2'-Q-Acetyl-3-declaidinosM 1, 12-dideoxy-6-Q-allyl-12,11-foxycarbonyl- (cyano) -methylene-erythromycin y4 To a solution of intermediate 37 (1.3 g) in anhydrous DMF (40 mL), potassium cyanide (0.500 g) was added under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 hour, quenched with an aqueous solution of 5% NaHCO 3 (50 mL), and extracted with DCM (2x50 mL). The crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH 95 \ 4 \ 0.01), to give the title compound (0.42 g). m \ z (ÍMHf) = 707.

INTERMEDIARY 39 2'-Q-Acetyl-12-azidoethanoyl-3-declaidinosyl-11-deoxy-10,11-didehydro-6 -? - allyl-erythromycin A To a solution of intermediate 37 (1.42 g) in anhydrous DMF (110 mL), sodium azide (0.2 1 g) was added under a nitrogen atmosphere. The mixture was heated at 80 ° C for 10 minutes, then quenched with water (100 mL) and extracted with EtOAc (3x200 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (1.36 g). m \ z ([IvIHf) = 723.

INTERMEDIARY 40 2'-Q-Acetyl-12-aminoethanoyl-3-declaidinosyl-11-deoxy-10,11-didehydro-6 -? - allyl-erythromycin A To a solution of intermediate 39 (1.36 g) in THF (25 mL), triphenylphosphine (0.985 g) and water (0.034 mL) were added. The mixture was stirred at room temperature overnight. After evaporating the solvent, the residue was dissolved in DCM (100 mL), and the solution was washed with water (2x100). The organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound (1.30 g). m \ z ([MH] +) = 697.

INTERMEDIARY 41 2'-0-Acetyl-12- (benzhydrylidene) -aminoethanyl-3-declaidinosyl-11-deoxy-10,11-didehydro-6-O-allyl-erythromycin A A solution of intermediate 40 (1.30 g) and benzophenone imine (0.9 mL) in anhydrous DCM (15 mL) was stirred at room temperature under nitrogen atmosphere. After 30 hours, the reaction was quenched with water (50 mL) and extracted with DCM (3x100 mL). The organic layer was dried over Na 2 SO 4, filtered and concentrated under vacuum to give the title compound (1.60 g). m \ z ([MH] +) = 861.

INTERMEDIARY 42 (11 S21?, A-2'-0-Acetyl-3-declaidyrosyl-11, 12-d-deoxy-6-Q-allyl-12,11-roxycarbonyl- (benzhydrideidenoamino) -methylene-1-erythromycin A A solution of intermediate 41 (1.60 g) and DBU (0.3 mL) in acetonitrile (90 mL) and water (9 mL) was stirred at room temperature for 2 hours. Then the solvents were evaporated, and the crude material was dissolved in DCM (100 mL). The mixture was washed with water (2x100 mL), and the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH3 9.5 \ 0.4 \ 0.03), to give the title compound (0.528 g). m \ z ([MH] +) = 861.

INTERMEDIARY 43 (4-pir8din-3-iM / imidazol-1-yl) methyl acetate To a stirred suspension of sodium hydride (0.769 g) in anhydrous DMF (30 mL) under nitrogen atmosphere, a solution of 3- (1-imidazol-4-yl) -pyridine (3 g) was added dropwise at room temperature. ) in anhydrous DMF (10 mL). The mixture was stirred for 30 minutes, and then methyl bromoacetate (2.4 mL) was added dropwise. After stirring for 2 hours, the solvent was evaporated under reduced pressure, and the residue was diluted with EtOAc (200 mL) and washed with water (50 mL). The aqueous phase was further extracted with EtOAc (2x40 mL). The organic layer was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (2.78 g). m \ z ([MHD = 218.

INTERMEDIARY 44 3- (4-pyridin-3-yl-1y ^ imidazole-1-yl) -propylonate methyl To a stirred suspension of sodium hydride (0.165 g) in anhydrous DMF (2.5 mL) cooled to 0 ° C, a solution of 3- (1 / imidazol-4-yl) -pyridine was added dropwise under nitrogen atmosphere. (1 g) in anhydrous DMF (5 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of methyl 3-bromopropanoate (0.830 mL) in anhydrous DMF (5 mL) was added dropwise. After stirring for 2 hours at 70 ° C, the solvent was evaporated under reduced pressure, the residue was diluted with EtOAc (50 mL), and washed with water (15 mL). The aqueous phase was further extracted with EtOAc (3x15 mL). The combined organic layers were dried over Na2SO4, concentrated under reduced pressure, and the crude product was purified by flash chromatography (eluting with: DCMWleOH from 95 \ 5 to 90 \ 10), to give the title compound (0.530 g ). m \ z ([MHf) = 232.

INTERMEDIARY 45 4- (4-pyridin-3-yl-1 > ^ midazol-1-yl) methyl butyrate To a stirred suspension of sodium hydride (0.745 g) in anhydrous DMF (8 mL) cooled to 0 ° C, a solution of 3- (1 / midazol-4-yl) - was added dropwise under nitrogen atmosphere pyridine (3 g) in anhydrous DMF (16 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of methyl 4-chlorobutanoate (2.76 mL) in anhydrous DMF (16 mL) was added dropwise. After stirring for 2.5 hours at 70 ° C, the solvent was evaporated under reduced pressure, and the residue was diluted with EtOAc (150 mL) and washed with water (50 mL). The aqueous phase was further extracted with EtOAc (3x40 mL). The combined organic layers were dried over Na 2 SO 4, concentrated under reduced pressure, and the crude product was purified by flash chromatography (eluting with: DCMWleOH 96 4), to give the title compound (2.2 g). m \ z ([MH] +) = 246.

INTERMEDIARY 46 5- (4-pyridin-3-yl-1 > y-imidazol-1-yl) pentanoate methyl To a stirred suspension of sodium hydride (0.745 g) in anhydrous DMF (8 mL) cooled to 0 ° C, a solution of 3- (1 / midazol-4-yl) - was added dropwise under nitrogen atmosphere pyridine (3 g) in anhydrous DMF (16 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of methyl 5-bromo-pentanoate (3.55 mL) in anhydrous DMF (16 mL) was added dropwise. After stirring for 2 hours at 70 ° C, the solvent was evaporated under reduced pressure, and the residue was diluted with EtOAc (150 mL) and washed with water (50 mL). The aqueous phase was further extracted with EtOAc (3x40 mL). The combined organic layers were dried over Na 2 SO 4, concentrated under reduced pressure, and the crude product was purified by flash chromatography (eluting with: DCMWleOH 96 4), to give the title compound (4.25 g). m \ z ([MH] +) = 260.

INTERMEDIARY 47 (4-Pir! Din-3-yl-imidazol-1-yl) -acetate sodium To a solution of intermediate 43 (0.100 g) in acetone (2 mL) at room temperature, an aqueous solution of 1 M NaOH (0.46 mL) was added. The mixture was stirred at room temperature for 20 hours, and then refluxed for 8 hours. Evaporation of the solvent under reduced pressure gave the title compound (0.100 g). m \ z ([H] +) = 204.

INTERMEDIARY 48 3- (4-Pir! Din-3-yl-imidazol-1-yl) -propionate sodium To a solution of intermediate 44 (0.100 g) in acetone (1 mL) at room temperature, an aqueous solution of 1 M NaOH (0.43 mL) was added. The mixture was stirred at room temperature for 6 hours. Evaporation of the solvent under reduced pressure gave the title compound (0.099 g). m \ z ([Hf) = 218.

INTERMEDIARY 49 4- (4-Pyridin-3-yl-imidazol-1-yl) -butyrate sodium To a solution of intermediate 45 (0.100 g) in acetone (1 ml_) at room temperature, an aqueous solution of NaOH to M (0.40 ml_) was added. The mixture was stirred at room temperature for 6 hours. Evaporation of the solvent under reduced pressure gave the title compound (0.096 g). m \ z ([H] +) = 232.

INTERMEDIARY 50 5- (4-Pyridin-3-yl-imidazol-1-yl) -pentanoate sodium To a solution of intermediate 46 (0.100 g) in acetone (1 mL) at room temperature, an aqueous solution of 1 M NaOH (0.38 mL) was added. The mixture was stirred at room temperature for 3 hours. Evaporation of the solvent under reduced pressure gave the title compound (0.095 g). m \ z (fMHf) = 246.

INTERMEDIARY 51 1 -Metox! -2- (4-pyridin-3-yl-1 / y-imldazol-1 -i-ethanol To a stirred suspension of sodium hydride (0.166 g) in anhydrous DMF (3 mL) cooled to 0 ° C, a solution of S-Z / imidazoM-i-pyridine (1 g) was added dropwise under nitrogen atmosphere. in anhydrous DMF (5 mL). The reaction mixture was allowed to reach room temperature, and after 15 minutes a solution of bromoacetaldehyde dimethyl acetal (0.816 mL) in anhydrous DMF (5 mL) was added dropwise. The reaction mixture was stirred at 70 ° C for 4 hours, and at room temperature overnight. After evaporating the solvent under reduced pressure, the crude material was purified by flash chromatography (eluting with DCM \ MeOH 90 \ 10), to give the title compound (1.15 g). m \ z ([MH] +) = 234. TLC: DCMWleOH 90 \ 10 (Rf = 0.5).

INTERMEDIARY 52 3- (4-Pyridin-3-ü-1 / nmidazoM -iQpropionaldehyde To a solution of 3- (1-imidazol-4-yl) -pyridine (0.350 g) in anhydrous THF (15 mL) cooled to 0 ° C, acrialdehyde (0.540 mL) was added dropwise. The resulting solution was stirred at room temperature for 3 days.

Evaporation of the solvent under reduced pressure gave the title compound (0.460 g). m \ z ([H] +) = 202.

INTERMEDIARY 53 4- (4-Pyridin-3-yl-1 / imidazol-1H) butan-1 -ol To a solution of intermediate 45 (1.2 g) in anhydrous THF (20 mL) cooled to 0 ° C, lithium aluminum hydride (1 M in THF) was added dropwise under nitrogen.2.55 mL). The reaction mixture was stirred for 2 hours at room temperature, and then water (30 mL) and EtOAc (75 mL) were added. The solvents were evaporated under reduced pressure, and the residue was extracted with EtOAc (2x75 mL). The combined organic layers were washed with saturated aqueous sodium potassium tartrate solution (80 mL), dried over Na 2 SO 4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (0.600 g). m \ z ([MH] +) = 218.

INTERMEDIARY 54 4- (4-Pirldin-3-yl-1 / flmidazol-1 -iQbutyraldehyde To a solution of oxalyl chloride (0.225 mL) in anhydrous DCM (7 mL) cooled to -78 ° C under nitrogen atmosphere, a solution of DMSO (0.275 mL) in anhydrous DCM (2 mL) was slowly added. After 15 min at -78 ° C, a solution of intermediate 53 (0.280 g) in anhydrous DCM (5 mL) was dripped within 30 minutes. The mixture was stirred at -40 ° C for 4 hours, and then TEA (0.900 mL) was added. The reaction was allowed to reach room temperature, and then water (10 mL) was added. The mixture was extracted with DCM (3x20 mL), the organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound (0.052 g). m \ z ([MH] +) = 216.

INTERMEDIARY 55 5- (4-Pyridin-3-yl-1 yy-imidazol-1-yl) pentan-1 -ol To a solution of intermediate 46 (3.54 g) in anhydrous THF (40 mL) cooled to 0 ° C, lithium aluminum hydride (1M in THF, 7.8 mL) was added dropwise under nitrogen. The reaction mixture was stirred for 2.5 hours at room temperature, and then water (50 mL), EtOAc (100 mL) and an aqueous solution of NH4OH at 28% were added until pH = 9. The solvents were evaporated under reduced pressure, and the residue was dissolved in EtOAc (2x100 mL). The solution was washed with saturated aqueous sodium potassium tartrate solution, dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DC WleOH from 95 \ 5 to 90 \ 10), to give the title compound (2.32 g). TLC: DCMWleOH 95 \ 5 (Rf = 0.18).

INTERMEDIARY 56 5-f4-Pyridin-3-yl-1 > Wmidazol-1-yl) pentanal To a solution of oxalyl chloride (0.755 mL) in anhydrous DCM (25 mL) cooled to -78 ° C under nitrogen atmosphere, a solution of DMSO (1.23 mL) in anhydrous DCM (8 mL) was slowly added. After 15 minutes at -78 ° C, a solution of intermediate 55 (1 g) in anhydrous DCM (18 mL) was added dropwise over 30 minutes. The mixture was stirred at -40 ° C for 3.5 hours, and then TEA (3.6 mL) was added. The reaction mixture was allowed to reach room temperature, and then water (50 mL) was added. The mixture was extracted with DCM (3x100 mL), the organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCMWleOH 92 \), to give the title compound (0.635 g). m \ z ([MHf) = 230.

INTERMEDIARY 57 4 - [(- f 2 { -2- ethoxyvinyl1quinoline To a solution of (methoxymethyl) triphenylphosphonium chloride (3.27 g) in anhydrous THF (60 mL) cooled to -78 ° C, sodium bis (trimethylsilyl) amide (1 M in THF, 9.5 mL) was added under nitrogen. , and the solution was stirred for 15 minutes. A solution of 4-qulnoline carboxaldehyde (1 g) in anhydrous THF (10 mL) was added, and the reaction mixture was stirred at -78 ° C for 30 minutes, at 0 ° C for 1.5 hours, and then at room temperature overnight. The reaction was quenched with water (50 mL), and extracted with EtOAc (75 mL). The aqueous phase was neutralized with saturated aqueous NH 4 Cl solution (50 mL), and extracted again with EtOAc (2x75 mL). The combined organic layers were dried over Na 2 SO 4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: Hexane / EtOAc from 60 40 to 50:50), to give the title compound ( 0.905 g). m \ z ([MHf) = 186.

INTERMEDIARY 58 4-F3- (1,3-D¡oxolan-2-yl) propinquinoline To a solution of [2- (1, 3-dioxolan-2-yl) -ethyl] -triphenylphosphonium bromide (10.6 g) in anhydrous THF (150 mL) cooled to -78 C, added dropwise under nitrogen atmosphere a solution of sodium bis (trimethylsilyl) amide (1M in THF, 23.9 mL). The mixture was stirred at -78 ° C for 30 minutes, and then a solution of 4-quinoline carboxaldehyde (2.5 g) in anhydrous THF (30 mL) was added. The mixture was allowed to reach room temperature, DBU (1.8 mL) was added, and the mixture was stirred for 6 hours at 50 ° C. The reaction was quenched with a saturated aqueous solution of NH CI (100 mL), and extracted with EtOAc (3x150 mL). The organic phase was dried over Na2SC >; 4, concentrated under reduced pressure, and the crude material was filtered on a silica pad (eluting with: cyclohexane \ EtOAc 70 \ 30). After evaporating the solvent under reduced pressure, the residue was dissolved in MeOH (20 mL), palladium (10% by weight on carbon powder, 0.360 g) was added, and the mixture was stirred under a hydrogen atmosphere (1.5 atmospheres) for 2 hours. The mixture was filtered through a pad of celite eluting with MeOH (2x100 mL), and purification by flash chromatography (eluting with: Et20), gave the title compound (0.700 g). m \ z ([MHf) = 244.

INTERMEDIARY 59 4-Quinolin-4-yl-but! Raldehyde To a solution of intermediate 58 (0.500 g) in acetone (5 mL), an aqueous solution of 2N HCl (5 mL) was added, and the mixture was stirred at 50 ° C for 2 hours. After evaporation of the solvent under reduced pressure, NH 4 OH was added to the residue until pH = 9. The aqueous solution was extracted with DCM (2x35 mL), and the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: EtOAc \ cyclohexane 80 \ 20), to give the title compound (0.315 g). m \ z ([MH] +) = 200.

INTERMEDIARY 60 4-Quinolin-4-yl-butyric acid To a solution of intermediate 59 (0.160 g) in acetone (4 mL), potassium permanganate (0.063 g) was added portionwise within 1 hour. After evaporation of the solvent, water (4 mL) was added, and the mixture was refluxed for 30 minutes. The reaction mixture was slowly cooled to 0 ° C, and kept at 0 ° C overnight. The reaction mixture was filtered through a pad of celite eluting with DCM (5 mL), and after removing the solvent under vacuum, the crude product was purified by flash chromatography (eluting with: DCMWleOH 90? 10), to give the title compound (0.050 g). m \ z ([MH] +) = 216.

INTERMEDIARY 61 ethyl 5-quinolin-4-yl-pentanoate To a stirred suspension of [3- (ethoxycarbonyl) -propyl] -triphenylphosphonium bromide (5.6 g) in anhydrous THF (100 mL) cooled to -78 ° C was added dropwise under a nitrogen atmosphere a solution of bis ( sodium trimethylsilyl) (1 M in THF, 12 mL). The mixture was stirred at -78 ° C for 1 hour, and then a solution of 4-quinoline carboxaldehyde (1.6 g) in anhydrous THF (15 mL) was dripped. The mixture was allowed to reach room temperature, stirred for 2 hours, then heated to 50 ° C, and stirred for 4 hours. The reaction was quenched with saturated aqueous NH 4 Cl solution (50 mL), and extracted with EtOAc (3x100 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by filtration on a pad of silica gel (eluting with: cyclohexane \ EtOAc 70 \ 30). After evaporating the solvent under reduced pressure, the residue was dissolved in MeOH (10 mL), palladium (10% by weight on carbon powder, 0.060 g) was added, and the mixture was stirred under a hydrogen atmosphere (1.5 atmospheres). ) for 1 hour. The mixture was filtered through a pad of celite eluting with MeOH (2x50 mL), and then evaporation of the solvent under reduced pressure gave the title compound (0.860 g). m \ z ([MH] +) = 258.

INTERMEDIARY 62 5-Quinolin-4-yl-pentanoic acid To a solution of intermediate 61 (0.194 g) in acetone (1 mL) at room temperature, an aqueous solution of 1 M NaOH (0.78 mL) was added. The mixture was refluxed for 2 hours. Evaporation of the solvent under reduced pressure gave the title compound (0.181 g). m \ z ([H] +) = 230.

INTERMEDIARY 63 5-Quinolin-4-yl-pentanal To a solution of intermediate 61 (0.050 g) in anhydrous toluene (1 mL) cooled to -78 ° C, diisobutylaluminum hydride (1M sol in toluene, 0.39 mL) was added slowly. The reaction mixture was stirred for 1 hour at -78 ° C, and then quenched with 2 mL of a mixture of water (0.25 mL), acetic acid (1 mL) and Et20 (3 mL) at -78 ° C. The temperature was allowed to reach room temperature, and then the crude material was filtered through a pad of celite eluting with DCM (3x10 mL). The organic phase was dried over Na 2 SO 4 and concentrated under reduced pressure to give e! compound of the title (0.040 g). m \ z ([MH] +) = 214.

INTERMEDIARY 64 3- (4-phen8l-1 y-imidazole-1-methylpropionate) To a stirred suspension of sodium hydride (0.017 g) in anhydrous DMF (0.250 mL) cooled to 0 ° C, a solution of 4-phenyl-1 ^ imidazole (0.100 g) in DMF was added dropwise under nitrogen atmosphere. anhydrous (0.8 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of 3-bromo-propionic acid methyl ester (0.083 mL) in anhydrous DMF (0.3 mL) was added dropwise. After stirring for 2 hours at 70 ° C, the solvent was evaporated under reduced pressure, and the residue was diluted with EtOAc (5 mL) and washed with water (3 mL). The aqueous phase was further extracted with EtOAc (3x5 mL). The combined organic layers were dried over Na2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 95 \ 5), to give the title compound ( 0.128 g). m \ z ([MH] +) = 231.

INTERMEDIARY 65 3- (4-Phenyl-imidazol-1-l) -propionate sodium To a solution of intermediate 64 (0.034 g) in acetone (0.50 mL) at room temperature, an aqueous solution of NaOH at 1 (0.15 mL) was added. The mixture was stirred at room temperature for 3 hours. Evaporation of the solvent under reduced pressure gave the title compound (0.035 g). m \ z ([H) = 217.

INTERMEDIARY 66 (4-phenyM / flmidazoM-yl) methyl acetate To a stirred suspension of sodium hydride (0.037 g) in anhydrous DMF (0.550 mL) cooled to 0 ° C, a 4-phenol-1 / imidazole solution (0.200 g) was added dropwise under nitrogen atmosphere. in anhydrous DMF (1.6 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of 2-chloroacetic acid methyl ester (0.134 mL) in anhydrous DMF (0.60 mL) was added dropwise. After stirring for 2 hours at 70 ° C, and overnight at room temperature, the mixture was diluted with Et20 (25 mL) and washed with water (10 mL). The aqueous phase was further extracted with Et20 (3x15 mL). The collected organic extracts were dried over Na 2 SO 4, concentrated under reduced pressure, and the crude product was purified by flash chromatography (eluting with: DCM VleOH from 100 0 to 96 4), to give the title compound (0.210). g). m \ z ([MH] +) = 217.

INTERMEDIARY 67 3- (4-Phenyl-imidazol-1-yl) -propionate sodium To a solution of intermediate 66 (0.190 g) in acetone (2.5 mL) at room temperature, an aqueous solution of NaOH at 1.2M (0.730 mL) was added. The mixture was stirred at room temperature for 2.5 hours, and then evaporation of the solvent under reduced pressure gave the title compound (0.205 g). m \ z ([MH] +) = 203.

INTERMEDIARY 68 3- (4-t! En-2-yl-1yyH'midazol-1-yl) methyl propionate To a stirred suspension of sodium hydride (0.013 g) in anhydrous DMF (0.250 mL) cooled to 0 ° C, a solution of 4-thiophen-2-yl-1 imidazole (0.100 g) was added dropwise under nitrogen atmosphere. ) in anhydrous DMF (1.6 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of methyl 3-bromopropionate (0.100 mL) in anhydrous DMF (0.3 mL) was added dropwise. After stirring for 5 hours at 70 ° C and overnight at room temperature, the solvent was evaporated under reduced pressure, the residue was dissolved with EtOAc (5 mL), and the solution was washed with water (3 mL). The aqueous phase was further extracted with EtOAc (3x5 mL). The combined organic layers were dried over a2SO4, concentrated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 95 \ 5), to give the title compound ( 0.013 g). m \ z ([MH] +) = 237.

INTERMEDIARY 69 3- (4-tien-2-l-1 / nmidazol-1-yl) sodium propionate To a solution of intermediate 68 (0.013 g) in acetone (0.3 mL) at room temperature, an aqueous solution of 1 M NaOH (0.055 mL) was added. The mixture was stirred at room temperature for 5 hours, and then evaporation of the solvent under reduced pressure gave the title compound (0.012 g). m \ z ([MH] +) = 223.

INTERMEDIARY 70 3- (3-thiazol-2-yl-pyrazol-1-yl) -propionate sodium To a stirred suspension of sodium hydride (0.016 g) in anhydrous DMF (0.3 mL) cooled to 0 ° C, a solution of 2- (1 // pyrazol-3-yl) was added dropwise under nitrogen atmosphere - thiazole (0.100 g) in anhydrous DMF (0.8 mL). The mixture was stirred for 15 minutes at room temperature, and then a solution of 3-bromo-propionic acid methyl ester (0.080 mL) in anhydrous DMF (0.3 mL) was added dropwise. After stirring for 4 hours at 70 ° C, the solvent was evaporated under reduced pressure, and the residue was diluted with EtOAc (5 mL) and washed with water (3 mL). The aqueous phase was further extracted with EtOAc (3x5 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude material was dissolved in acetone (1 mL) and an aqueous solution of NaOH at 1.2 N (0.55 mL) was added. The mixture was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.025 g). m \ z ([MH] +) = 224.

INTERMEDIARY 71 r (3-methoxy-cyanoxalin-2-yl) thio-1-ethyl acetate To a solution of 2-chloro-3-methoxy-quinoxaline (0.100 g) in anhydrous DMF (3 mL), potassium carbonate (0.142 g) and mercaptoacetic acid ethyl ester (0.084 mL) were added, and the mixture The resulting mixture was stirred at 80 ° C for 1.5 hours. The solvent was removed under reduced pressure, water (5 mL) was added, and the mixture was extracted with EtOAc (3x10 mL). The combined organic phases were washed with brine (5 mL), dried over Na 2 SO 4, and evaporated under reduced pressure. The crude material was purified by flash chromatography (eluting with: cyclohexane \ EtOAc 80 \ 20), to give the title compound (0.065 g). m \ z ([MH] +) = 255. TLC: cyclohexane \ EtOAc 80 \ 20 (Rf = 0.57).

INTERMEDIARY 72 f (3-Methoxy-cyanoxalin-2-yl) thio-acetic acid To a solution of intermediate 71 (0.060 g) in THF (2 mL), an aqueous solution of 3 N NaOH (2 mL) was added. The mixture was stirred vigorously at room temperature overnight, and then after evaporation of the solvent, an aqueous solution of 1 N HCl was added until pH = 1. The solution was extracted with DCM (3x8 mL), the organic phase was washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure, to give the title compound (0.045 g). m \ z ([MH] +) = 227. TLC: EtOAc \ MeOH 98 \ 2 (Rf = 0.48).

INTERMEDIARY 73 (quinoxalin-2-yloxy) ethyl acetate To a solution of quinoxalin-2-ol (2 g) in acetone (30 mL), potassium carbonate (3.8 g) and chloroacetic acid ethyl ester (2.2 mL) were added, and the resulting mixture was stirred under reflux for 6 hours. hours. After evaporating the solvent under reduced pressure, water (30 mL) was added, and the mixture was extracted with EtOAc (3x50 mL). The organic phase was washed with brine (30 mL), dried over Na 2 SO 4 and evaporated under reduced pressure. The crude material was purified by flash chromatography (eluting with: cyclohexane \ EtOAc 3 \ 2), to give the title compound (1.5 g). m \ z ([MH] +) = 233.

INTERMEDIARY 74 Acid (Quinoxin-2-yl-oxy) acetic acid To a solution of intermediate 73 (0.300 g) in THF (10 mL), an aqueous solution of 3N NaOH (10 mL) was added. The mixture was stirred vigorously at room temperature for 1 hour, and then after evaporation of the solvent, an aqueous solution of 1 N HCl was added until pH = 1. The aqueous solution was extracted with DCM (3x20 mL), and the organic phase was washed with brine (0 mL), dried over Na2SO4 and concentrated under reduced pressure, to give the title compound (0.230 g). m \ z ([MHf) = 205.

INTERMEDIARY 75 3-r4- (3,5-Difluorophenyl) -1y¾¾irazol-1-propiopropionaldehyde To a solution of 4- (3,5-difluoro-phenyl) -1-pyrazole (0.050 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.050 mL) was added portionwise. The resulting solution was stirred at 55 ° C for 16 hours, and then the solvent was removed under reduced pressure, to give the title compound (0.52 g). m \ z ([MH] +) = 237.

INTERMEDIARY 76 3-f4- (4-Chlorophenyl) -2,5 iimethyl-1 jmidazol-1-inpropionaidehyde To a solution of 4- (4-chloro-phenyl) -2,5-dimethyl-1 imidazole (0.030 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.069 mL) was added portionwise. The resulting solution was stirred at 50 ° C for 24 hours, and then the solvent was removed under reduced pressure, to give the title compound (0.036 g). m \ z ([MH] +) = 263.

INTERMEDIARY 77 3-r4- (4-Nitrophenin-1-imidazol-1-yl-1-propionaldehyde To a solution of 4- (4-nitro-phenyl) -1 // imidazole (0.100 g) in anhydrous acetonitrile (12 mL), acrylaldehyde (0.450 mL) was added portionwise. The resulting solution was stirred at 50 ° C for 5 days. The solvent was removed under reduced pressure to give the title compound (0.120 g). m \ z ([MH] +) = 246.

INTERMEDIARY 78 3- (4-Pyridin-4-yl-imidazol-1-yl) -prop -onaldehyde To a solution of 4- (1-imidazol-4-yl) -pyridine (0.040 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.050 mL) was added portionwise. The resulting solution was stirred at 55 ° C for 8 hours, and at room temperature overnight. The solvent was removed under reduced pressure to give the title compound (0.42 g). m \ z ([MH] +) = 202.

INTERMEDIARY 79 3- (3-Trifluoromethyl-1i ^ pyrazol-4-yl) -propionaldehyde To a solution of oxalyl chloride (0.127 mL) in anhydrous DCM (4 mL) cooled to -78 ° C under nitrogen atmosphere, DIVISO (0.155 mL) was slowly added. After stirring for 30 minutes at -78 ° C, a solution of 3- (3-trifluoromethyl-1-yl (0.094 mL) in anhydrous DCM (3 mL) was added dropwise.The mixture was stirred at -40. C. for 3 hours, and then TEA (0.507 mL) was added.The reaction was allowed to reach room temperature, and then a saturated aqueous solution of NaHCO3 (10 mL) was added, and the mixture was extracted with DCM (3x10). mL) The organic phase was washed with brine (10 mL), dried over Na 2 SO 4 and concentrated under reduced pressure to give the title compound (0.100 g) m z ([MH] +) = 193.

INTERMEDIARY 80 3-r5-Methyl-4- (4-trifluoromethyl-phenyl) -imidazol-1-in-propionaldehyde To a solution of 5-methyl-4- (4-trifluoromethyl-phenyl) -1-imidazole (0.030 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.027 mL) was added. The resulting solution was stirred at 50 ° C for 24 hours, and at room temperature for 12 hours. The solvent was removed under reduced pressure to give the title compound (0.038 g). m \ z ([H] +) = 283.

INTERMEDIARY 81 3-Pyridin-3-α-propionaldehyde To a solution of oxalyl chloride (0.127 mL) in anhydrous DCM (4 mL) cooled to -78 ° C under nitrogen atmosphere, DMSO (0.155 mL) was slowly added. After 20 minutes at -78 ° C, a solution of 3-pyridin-3-yl-propan-1-ol (0.100 g) in anhydrous DCM (3 mL) was added dropwise within 30 minutes. The mixture was stirred at -40 ° C for 3 hours, and then TEA (0.507 mL) was added. The reaction was allowed to reach room temperature, and then water (5 mL) was added. The mixture was extracted with DCM (3x10 mL), and the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH of 100? 0 to 95? 5), to give the title compound (0.052 g). m \ z ([MH] +) = 136.

INTERMEDIARY 82 3- (4-Pyridin-2-yl-pyrazol-1 -iQ-proplonaldehyde To a solution of 2- (1-pyrazol-4-ii) -pyridine (0.058 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.022 mL) was added. The resulting solution was stirred at 50 ° C for 3 hours. The solvent was removed under reduced pressure to give the title compound (0.060 g). m \ z ([MH] +) = 202.

INTERMEDIARY 83 3-Pyridin-4-yl-propionaldehyde To a solution of oxalyl chloride (0.127 mL) in anhydrous DCM (3 mL) cooled to -70 ° C under nitrogen atmosphere, a solution of DMSO (0.155 mL) in anhydrous DCM (2 mL) was added dropwise. The reaction mixture was stirred for 30 minutes, and then a solution of 3-pyridin-4-yl-propan-1-ol (0.100 g) in anhydrous DCM (2 mL) was added dropwise in 30 minutes. The mixture was stirred at -60 ° C for 3 hours, and then the reaction mixture was allowed to reach -10 ° C and TEA (0.507 mL) was added. The reaction was stirred overnight reaching slowly to room temperature. Saturated aqueous solution of NaHCO 3 (5 mL) was added, and the organic phase was dried over Na 2 SO 4 and concentrated under reduced pressure, to give the title compound (0.100 g). m \ z ([H] +) = 136.

INTERMEDIARY 84 3- (4-Pyrimidin-4-yl-pyrazol-1-yl) -propionaldehyde To a solution of 4- (1 / p -razol-4-yl) -pyrimidine (0.022 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.020 mL) was added. The reaction mixture was stirred at 50 ° C for 1.5 hours. The solvent was removed under reduced pressure to give the title compound (0.025 g). m \ z ([MH] +) = 203.

INTERMEDIARY 85 3- (4-Pyridin-4-yl-pyrazol-1 -ID-propionaldehyde To a solution of 2- (1-pyrazol-4-yl) -pyridine (0.050 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.220 mL) was added. The resulting solution was stirred at 50 ° C for 4 hours and at room temperature overnight. The solvent was removed under reduced pressure to give the title compound (0.050 g). m \ z ([MH] +) = 202.

INTERMEDIARY 86 S - ^ - Q ^ -Dicloro-feniD ^^ - dimethyl-lmidazol-l -ill-propionaldehyde To a solution of 4- (3,5-dichloro-phenyl) -2,5-d-methyl-1-midazole (0.035 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.116 mL) was added in portions. The resulting solution was stirred at 50 ° C for 56 hours. The solvent was removed under reduced pressure to give the title compound (0.029 g). m \ z ([MH] +) = 297.

INTERMEDIARY 87 3- [2,5-Dimethyl-4- (3-trifluoromethyl-phenyl) -imidazol-1-n-propionaldehyde To a solution of 2,5-dimethyl-4- (3-trifluoromethyl-phenyl) -1 ^ imidazole (0.037 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.120 mL) was added in portions. The resulting solution was stirred at 50 ° C for 48 hours. The solvent was removed under reduced pressure to give the title compound (0.042 g). m \ z ([MH] +) = 297.

INTERMEDIARY 88 3-G4- (1, 3-benzoxazol-2-yl) -1 and ^ pyrazol-1 -ill-propionaldehyde To a stirred suspension of 2- (1 / pyrazol-4-yl) -1,3-benzoxazole (0.053 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.220 mL) was added. The reaction mixture was stirred at 50 ° C for 6 hours. After filtration, the solvent was removed under reduced pressure, to give the title compound (0.034 g). m \ z ([Hf) = 242.

INTERMEDIARY 89 3- (5-Pyridin-4-yl-pyrazol-1-yl) -propionaldehyde To a solution of 4- (1/7-pyrazol-3-yl) -pyridine (0.030 g) in anhydrous acetonitrile (1 mL), acrylaldehyde (0.085 mL) was added. The reaction mixture was stirred at 50 ° C for 48 hours. The solvent was removed under reduced pressure to give the title compound (0.036 g). m \ z ([MHf) = 202.

INTERMEDIARY 90 3-f2-Pridine-4-yl-imidazol-1-yl) -propionaldehyde To a solution of 4- (1-midazol-2-yl) -pyridine (0.050 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.080 mL) was added. The reaction mixture was stirred at 50 ° C for 14 hours. The solvent was removed under reduced pressure to give the title compound (0.050 g). m \ z ([MH] +) = 202.

INTERMEDIARY 91 3- (4-quinolin-2-yl-1? Pyrazol-1 -iP-propionaldehyde To a solution of 2- (1-pyrrazol-4-yl) quinoline (0.050 g) in anhydrous acetonitrile (5 mL), acrylaldehyde (0.116 mL) was added. The reaction mixture was stirred at 50 ° C for 3 days. The solvent was removed under reduced pressure to give the title compound (0.050 g). m \ z ([MH] +) = 252.

INTERMEDIARY 92 3- (4-QuSnolin ^ 4-yl-1 > ypyrazole-1-in-propionaldehyde To a solution of 4- (1 / pyrazol-4-yl) quinoline (0.050 g) in anhydrous acetonitrile (4 mL), acrylaldehyde (0.260 mL) was added. The reaction mixture was stirred at 50 ° C for 7 days. The solvent was removed under reduced pressure to give the title compound (0.050 g). m \ z ([MH] +) = 252.

INTERMEDIARY 93 3-f4-Quinoxalin-2-yl-1 > ypyrazol-1-in-propylonaldehyde To a solution of 2- (1 / plrazol-4-yl) quinoxaline (0.050 g) in anhydrous acetonitrile (4 mL), acrylaldehyde (0.156 mL) was added. The reaction mixture was stirred at 50 ° C for 3 days. The solvent was removed under reduced pressure to give the title compound (0.050 g). m \ z ([MH] +) = 253.

INTERMEDIARY 94 3-Tien-3-yl-propionaldehyde To a solution of oxalyl chloride (0.190 mL) in anhydrous DCM (6 mL) cooled to -78 ° C under nitrogen atmosphere, a solution of DMSO (0.230 mL) in anhydrous DCM (4 mL) was slowly added. After stirring for 30 minutes at -78 ° C, a solution of 3-thien-3-ylpropan-1-ol (0.150 g) in anhydrous DCM (4 mL) was added dropwise. The mixture was stirred at -40 ° C for 3 hours, and then TEA (0.750 mL) was added. The reaction was allowed to reach room temperature, and then saturated aqueous NaHCO3 solution (10 mL) was added, and the mixture was extracted with DCM (3x10 mL). The organic phase was washed with brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure to give the title compound (0.140 g). m \ z ([MHf) = 141.

INTERMEDIARY 95 3-r5- (3-Methyl-pyrazin-2-yl) -pyrazol-1-n-propionaldehyde To a solution of 2-methyl-3- (2-piyrazol-5-yl) -pyrazine (0.030 g) in anhydrous acetonitrile (1 mL), acrylaldehyde (0.065 mL) was added. The reaction mixture was stirred at 50 ° C for 60 hours. The solvent was removed under reduced pressure to give the title compound (0.038 g). m \ z ([MH] +) = 217.

INTERMEDIARY 96 3-G2- (MethylthioH-benzimidazol-1 - ?? - propionaldehyde To a solution of 2- (methylthio) -1 / benzimidazole (0.030 g) in anhydrous acetonitrile (1 mL), acriialdehyde (0.080 mL) was added. The reaction mixture was stirred at 50 ° C for 48 hours. The solvent was removed under reduced pressure to give the title compound (0.039 g). m \ z ([MHf) = 221.

INTERMEDIARY 97 3-r3- (4-Chlorophenyl) -1 ^ plrazol-5- ?? -propionaldehyde To a stirred suspension of Dessinin's periodinane (0.163 g) in anhydrous DCM (4 mL), 3- [3- (4-chlorophenyl) -1 / -pyrazolo-5-yl] propan-1-ol ( 0.050 g), and the mixture was stirred at room temperature overnight. The reaction was quenched with a Na 2 S 2 O 3 solution (5% in saturated aqueous solution of NaHCO 3, 3 mL), stirred for 1 hour, and then extracted with DCM (10 mL). The organic phase was washed with brine (5 mL), separated, dried over Na 2 SO 4 and concentrated under reduced pressure to give the title compound (0.040 g). m \ z ([MHf) = 235.

INTERMEDIARY 98 3-r6-fMethylthio) -7 ^ purln-7-in-propionaldehyde To a solution of 6- (methylthio) -7 / purine (0.032 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.040 mL) was added. The reaction mixture was stirred at 80 ° C for 8 hours and overnight at room temperature. The solvent was removed under reduced pressure to give the title compound (0.042 g). m \ z ([MH] +) = 223.

INTERMEDIARY 99 3- (6-Methoxy-7 / ^ purin-7-H) -propionaldehyde To a solution of 6-methoxy-7 purine (0.040 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.057 mL) was added. The reaction mixture was stirred at 80 ° C for 8 hours. The solvent was removed under reduced pressure to give the title compound (0.055 g). m \ z ([MH] +) = 207.

INTERMEDIARY 100 3- (6-Methoxy-2-oxo-1,3-benzoxazol-3 (2H) -l) -propionaldehyde To a solution of 6-methoxy-1,3-benzoxazole-2 (3H) -one (0.072 g) in anhydrous acetonitrile (2 mL), acnlaldehyde (0.060 mL) was added. The reaction mixture was stirred at 50 ° C for 3 hours. The solvent was removed under reduced pressure to give the title compound (0.080 g). m \ z ([MHf) = 222.

INTERMEDIARI0 101 3- (1 vyPirrolo [2,3- ^ pyridin-1-yl) -propionaldehyde To a solution of 1 pyrrolo [2,3- ^] pyridine (0.040 g) in anhydrous acetonitrile (3 mL), acnlaldehyde (0.071 mL) was added. The reaction mixture was stirred at 80 ° C for 6 hours, and then the solvent was removed under reduced pressure, to give the title compound (0.042 g). m \ z ([MH] +) = 175.

INTERMEDIARY 102 3-r3- (2,4-Dimethyl-1, 3-thiazol-5-in-1 / -pyrazol-l-1-propionaldehyde To a solution of 2,4-dimethyl-5- (1-pyrazol-3-yl) -1,3-thiazole (0.032 g) in anhydrous acetonitrile (1 mL), acnlaldehyde (0.040 mL) was added. The reaction mixture was stirred at 50 ° C for 5 hours, and then at room temperature for 3 days. Evaporation of the solvent under reduced pressure gave the title compound (0.042 g). m \ z ([MH] +) = 236.

INTERMEDIARY 103 3- (3H ^ midazo |, 5-¿pyridin-3-yl) propionaldehyde and 3- (1yy-jmldazor4,5-gjpiridin-1-yl) propionaldehyde To a solution of 3H-imidazo [4,5-β-pyridine (0.050 g) in anhydrous acetonitrile (4 mL), acrylaldehyde (0.025 mL) was added. The reaction mixture was stirred at 80 ° C overnight, and then the solvent was removed under reduced pressure, to give a 1 \ 1 mixture of the title compound (0.050 g). m \ z ([MH] +) = 176.

INTERMEDIARY 104 3- (1 / y-8encimidazol-1-yl) propionaldehyde To a solution of 1-benzimidazole (0.050 g) in anhydrous acetonitrile (4 mL), acrylaldehyde (0.160 mL) was added. The reaction mixture was stirred at 80 ° C overnight, and then the solvent was removed under reduced pressure, to give the title compound (0.050 g). m \ z ([MH] +) = 175.

INTERMEDIARI0 105 3- (3H-lmidazor4.5- ^ pir¡d¡n-3-yl) propionaldehyde To a solution of 3H-imidazo [4,5- ^] pyridine (0.050 g) in anhydrous acetonitrile (3 mL), acrylaldehyde (0.250 mL) was added. The reaction mixture was stirred at 80 ° C for 24 hours, and then the solvent was removed under reduced pressure, to give the title compound (0.050 g). m \ z ([H] +) = 176.

INTERMEDIARY 106 2- (3,3-Dimethoxy-propylsulfanine-quinoxaline) To a solution of 2-quinoxalinothiol (0.200 g) in a mixture of anhydrous dioxane \ DMF 4 \ 1 (5 mL), sodium hydride (80% mineral oil, 0.044 g) was added in portions under a nitrogen atmosphere, and the reaction mixture was stirred at room temperature for 15 minutes. Then, 3-bromopropionaldehyde dimethyl acetal (0.200 mL) was added, and the solution was heated at 80 ° C for 1.5 hours. After dilution to room temperature with EtOAc (5 mL), the solution was concentrated under reduced pressure, diluted with water (10 mL), and extracted with EtOAc (3x10 mL). The combined organic phases were then washed with brine (10 mL), dried over Na2SO4 and concentrated in vacuo, to give a crude material which was purified by flash chromatography (eluent: cyclohexane / EtOAc 3 \ 1), to give the title compound (0.280 g). m \ z ([H] +) = 265. TLC: Cyclohexane \ EtOAc 7 \ 3 (Rf = 0.47).

INTERMEDIARY 107 3- (4-Phenyl-1 // - imidazol-1 -iQpropionaldehyde To a solution of 4-phenyl-1/7 !: midazole (0.050 g) in anhydrous acetonitrile (4 mL), acrylaldehyde (0.210 mL) was added. The reaction mixture was stirred at 80 ° C for 24 hours, and then the solvent was removed under reduced pressure, to give the title compound (0.050 g). m \ z ([MH] +) = 201.

INTERMEDIARY 108 4-G1 - (2,2-Dimethoxyethyl) -1 yy-imidazoM-illpyridine To a stirred suspension of sodium hydride (0.009 g) in anhydrous DMF (0.5 mL), 4- (1 / -imidazol-4-yl) pyridine (0.040 g) was added under a nitrogen atmosphere, and the reaction mixture was added. stirred at room temperature for 30 minutes. Then, 2-bromoacetaldehyde dimetii aceta was added! (0.040 mL), and the solution was heated at 70 ° C for 8 hours. After cooling to room temperature, the solvent was evaporated to give the title compound (0.064 g). m z ([MH] +) = 234.

INTERMEDIARY 109 2- (2,2-Dimethoxy-ethylsulfanyl) -quinoxaline To a solution of 2-quinoxa! Inothiol (0.200 g) in an anhydrous dioxane-DMF 4 \ 1 mixture (5 mL), sodium hydride (80% mineral oil, 0.044 g) was added portionwise under nitrogen. , and the reaction mixture was stirred at room temperature for 15 minutes. Then, 2-bromoacetaldehyde dimethylacetal (0.175 mL) was added, and the solution was heated at 80 ° C for 4.5 hours. After dilution to room temperature with EtOAc (5 mL), the solution was concentrated under reduced pressure, diluted with water (10 mL), and extracted with EtOAc (3x10 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and evaporated under vacuum, yielding a crude product which was purified by flash chromatography (eluting with: Cyclohexane / EtOAc 3 \ 1) which gave the compound of the title (0.167 g). m \ z ([MH] +) = 251. TLC: Cyclohexane \ EtOAc 7 \ 3 (Rf = 0.52).

INTERMEDIARY 110 3-f4- (Tiofen-2-yl) -imidazoM-il) -propionic acid To a solution of 4-thiophen-2-yl-1 ^ imidazole (0.030 g) in anhydrous acetonitrile (3 mL), TEA (0.022 mL) was added. After stirring at room temperature for 15 minutes, acrylaldehyde (0.034 mL) was added dropwise, and the resulting solution was heated at 75 ° C for 8 hours, and then the solvent was removed under reduced pressure, to give the title compound. title (0.033 g). m \ z ([MH] +) = 207.

INTERMEDIARY 111 3- (6-Methyl-2-oxo-1,3-benzoxazol-3 (2H) -yl) propanal To a solution of 6-methyl-1,3-benzoxazole-2 (3H) -one (0.030 g) in anhydrous acetonitrile (2 mL), acrylaldehyde (0.060 mL) was added. The reaction mixture was stirred at 50 ° C for 48 hours, and then the solvent was removed under reduced pressure, to give the title compound (0.040 g). m \ z ([MHf) = 206.

INTERMEDIARY 112 4-G1 - (2,2-dimethoxyethyl) -1-imidazole-2-inpyridine To a stirred suspension of sodium hydride (0.009 g) in anhydrous DMF (0.5 mL), 4- (1-imidazol-2-yl) pyridine (0.040 g) was added under a nitrogen atmosphere, and the reaction mixture was stirred at room temperature for 30 minutes. Then, 2-bromoacetaldehyde dimethyl acetal (0.040 mL) was added, and the solution was heated at 70 ° C for 30 hours. After cooling to room temperature, the solvent was evaporated under vacuum to give the title compound (0.064 g). m \ z ([MH] +) = 234.

INTERMEDIARY 113 3,4-Dimethyl-5-ri- (3-oxopropyl) -1 > y-1,2 ^ To a solution of 3,4-dimethyl-5- (1 ^ 1, 2,4-triazol-3-yl) thiophene-2-carbonitrile (0.037 g) in anhydrous acetonitrile (1 mL), acrylaldehyde (0.040 mL) was added. ), and the resulting solution was heated at 50 ° C for 5 hours. Evaporation of the solvent under vacuum gave the title compound (0.046 g). m \ z ([MHf) = 261.

INTERMEDIARY 114 3-Quinolin-3-yl-propionaldehyde To a solution of oxalyl chloride (0.290 mL) in anhydrous DCM (8 mL) cooled to -78 ° C under nitrogen atmosphere, DMSO (0.340 mL) was slowly added. After 1 hour at -78 ° C, a solution of 3-quinolin-3-ylpropan-1-ol (0.300 g) in anhydrous DCM (3 mL) was added. After stirring at -40 ° C for 3 hours, TEA (0.892 mL) was added, and the reaction mixture was allowed to reach room temperature. Water (10 mL) was added, and the mixture was extracted with DCM (3x10 mL), the organic phase was dried over Na2SO4 and concentrated under reduced pressure, to give the title compound (0.290 g). m \ z ([MH] +) = 186.

INTERMEDIARI0 115 3-r4- (3-Nitrophenyl) -1 yy-imidazol-1-trimpropanal To a solution of 4- (3-nitrophenyl) -1-imidazole (0.040 g) in anhydrous acetonitrile (5 mL), acrylaldehyde (0.120 mL) was added, and the resulting solution was heated to 80 ° C and stirred for 4 days . The solvent was removed under reduced pressure to give the title compound (0.041 g). m \ z ([MH] +) = 246.

INTERMEDIARY 116 1 - (2,3-DihJdro-1, 4-benzodyloxy-6-yl) butane-1,4-diol To a solution of lithium aluminum hydride (1 M in THF, 9.53 mL) in anhydrous THF (15 mL) cooled to 0 ° C, a solution of 4- (2,3-dihydro-1) acid was added dropwise. , 4-benzodioxin-6-yl) -4-oxobutyric acid (0.750 g) in anhydrous THF (5 mL). The reaction mixture was heated to reflux for 24 hours, then cooled to room temperature, and diluted with EtOAc (10 mL). After evaporation of the solvent under reduced pressure, the crude material was treated with an aqueous solution of 1 N HCl (20 mL) and DCM (100 mL). The organic phase was washed with saturated aqueous solution of NaHCC > 3 (50 mL), brine (50 mL), dried over Na 2 SO 4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (EtOAc \ cyclohexane from 50 \ 50 to 100 \ 0), to give the title compound (0.340 g). m \ z ([MH] +) = 225.

INTERMEDIARY 117 4- (2,3-Dihydro-1! 4-benzodioxin-6-yl) -4-oxobutanal To a solution of oxalyl chloride (0.560 mL) in anhydrous DCM (5 mL) cooled to -78 ° C under nitrogen atmosphere, a solution of DMSO (0.910 mL) in anhydrous DCM (5 mL) was slowly added. After stirring for 30 minutes at -78 ° C, a solution of intermediate 116 (0.340 g) in anhydrous DCM (2 mL) was added dropwise. The reaction mixture was stirred at -40 ° C for 3 hours, then TEA (2.5 mL) was added, and then the reaction mixture was allowed to reach room temperature. Saturated aqueous NaHCO3 solution (20 mL) was added, and the mixture was extracted with DCM (3x20 mL). The organic phase was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (EtOA cyclohexane 40 \ 60) to give the title compound (0.250 g). m \ z ([H] +) = 221.

INTERMEDIARY 118 1-f2-f1.3-D-oxolan-2-yl) etin-5-methoxy-1yy 3-ar- rolor3,2-b1-pyridine To a solution of 5-methoxy-1-pyrrolo [3,2-b] pyridine (0.040 g) in Anhydrous THF (1.5 mL) cooled to 0 ° C, sodium hydride (0.010 g) was added under a nitrogen atmosphere. The mixture was stirred at room temperature for 1 hour, and then 2- (2-bromoethyl) -1,3-dioxolane (0.038 mL) was added, and stirring was continued for another 6 hours. The reaction mixture was quenched with water (3 mL) and extracted with DCM (3x5 mL), and the organic phase was dried over Na2SO4 and concentrated under reduced pressure, to give the title compound (0.067 g). m \ z ([MH] +) = 249.

INTERMEDIARY 119 2-? - (2,2-Pimetoxietll) -1 yy-pyrazol-3-ylM, 3-thiazole To a stirred suspension of sodium hydride (0.005 g) in anhydrous DMF (0.5 mL) at 0 ° C, under a nitrogen atmosphere, a solution of 2- (1 / pyrazole-3-yl) -1, 3 was added. -thiazole (0.030 g) in anhydrous DMF (1 mL). The mixture was allowed to reach room temperature, stirred for another 15 minutes, and then a solution of bromoacetaldehyde dimethyl acetal (0.024 mL) in anhydrous DMF (0.5 mL) was added. After stirring the reaction mixture at room temperature for 24 hours, the solvent was evaporated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM), to give the title compound (0.015 g ). m \ z ([MH] +) = 240.

INTERMEDIARY 120 1 - (2,2-Di methoxyethyl) "4-phenyl-1 / imidazoi To a stirred suspension of sodium hydride (0.005 g) in anhydrous DMF (0.7 mL) at 0 ° C, a solution of 4-phenyl-1 / imidazole (0.023 g) in anhydrous DMF (1 mL) was added under a nitrogen atmosphere. ). The mixture was allowed to reach room temperature, stirred for another 15 minutes, and then a solution of bromoacetaldehyde dimethyl acetal (0.022 mL) in anhydrous DMF (0.7 mL) was added. After stirring the reaction mixture at room temperature for 24 hours, the solvent was evaporated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 90 \ 10) , to give the title compound (0.027 g). m \ z ([MH] +) = 233.

INTERMEDIARY 121 1 - (2,2-Dimethoxyethyl) -4-t-ene-2-l-1 ^ midazole To a stirred suspension of sodium hydride (0.019 g) in anhydrous DMF (3 mL) at 0 ° C, under a nitrogen atmosphere, a solution of 4-thien-2-yl-1 imidazole (0.100 g) in DMF was added. anhydrous (1 mL). The mixture was allowed to reach room temperature, stirred for another 15 minutes, and then a solution of bromoacetaldehyde dimethyl acetal (0.090 mL) in anhydrous DMF (1 mL) was added. After stirring at room temperature for 24 hours, the solvent was evaporated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 99 \ 1), to give the title compound (0.088 g). m \ z ([MH] +) = 239.

EXAMPLE 1 III-L-O-Acetyl-S-Decladinosyl-II.IZ-dideoxy-e-O-methyl-a-oxo-12,11-foxycarbonyl-cyano) -methylene-erythromycin A To a solution of intermediate 3 (0.060 g) in anhydrous DMF (16 mL), potassium cyanide (0.051 g) was added under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 hours, quenched with saturated aqueous solution of NaHCO3 (30 mL), and extracted with DC (3x30 mL). The organic phase was then washed with brine (30 mL), dried over Na 2 SO 4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (0.017 g). 1 H-NMR (CDCl 3) d: 5.27 (dd, 1 H), 4.74 (dd, 1 H), 4.62 (d, 1 H), 4.42 (d, 1 H), 4.26 (d, 1 H), 3.84 ( q, 1 H), 3.56 (m, 1 H), 3.16 (m, 1 H), 3.10-3.0 (m, 2H), 2.77 (s, 3 H), 2.68 (m, 1 H), 2.60 (m , 1 H), 2.25 (s, 6 H), 2.05 (m, 3 H), 1.90 (m, 1 H), 1.68 (m, 1 H), 1.63 (m, 2H), 1.56 (s, 3 H) ), 1.39 (d, 3 H), 1.35 (m, 1 H), 1.30 (s, 3 H), 1.26 (d, 3 H), 1.18 (d, 3 H), 1 .14 (d, 3 H) ), 1.06 (d, 3 H), 0.92 (t, 3 H). TLC: DCMVMeOH 95 \ 5 (Rf = 0.57).

EXAMPLE 2 (H ^ I-S-Decadinosil-II.IZ-dideoxy-B-O-methyl-S-oxo-i. H -roxycarbonyl- (cyano) -methylene T-erythromycin A A solution of Example 1 (0.024 g) in MeOH (1 mL) was stirred for 24 hours, and then concentrated under reduced pressure, to give the title compound (0.020 g). H-NMR (CDCIs) d: 5.26 (dd, 1H), 4.61 (d, 1H), 4.34 (d, 1H), 4.28 (m, 1H), 3.87 (q, 1H), 3.57 (m, 1H), 3.18 (m, 1H), 3.15 (t, 1H), 3.12 (m, 1H), 3.06 (m, 1H), 2.78 (s, 3 H), 2.62 (m, 1H), 2.46 (m, 1H), 2.27 (s, 6 H), 1.91 (m, 1H), 1.84 (m, 1H), 1.70 (m, 1H), 1.68 (m, 1H), 1.62 (m, 1H), 1.57 (s, 3 H) , 1.41 (d, 3 H), 1.34 (d, 3 H), 1.34 (s, 3 H), 1.24 (m, 1 H), 1.26 (d, 3 H), 1.14 (d, 3 H), 1.07 ( d, 3 H), 0.92 (t, 3 H). TLC: DCMWleOH 90? 10 (Rf = 0.38).

EXAMPLE 3 (11: 21 ¾-2'-0-Acetyl-3-declaidinosii-11,12-dideoxy-6-0-methyl-3-oxo-2,11-foxycarbonyl- (aminometii) -rnetylene -T-erythromycin TO To a solution of intermediate 4 (0.036 g) in PrOH (1.5 mL), sodium cyanoborohydride (0.023 g) and titanium chloride (III) (10 wt% solution in hydrochloric acid) were added portionwise within 6 hours. at 20 30 30% by weight, 0.1 mL). The mixture was diluted with saturated aqueous NaHCO3 solution (3x2 mL), and extracted with DCM (3x2 mL). The organic phase was dried over a2SO4, and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH 100 \ 0 \ 0, 98 \ 2 \ 0, 95 \ 5 \ 0.5), to give the title compound (0.010 g). 1 H-NMR (CDCl 3) d: 5.06 (dd, 1 H), 4.76 (dd, H), 4.38 (d, 1 H), 4.17 (d, 1 H), 3.80 (q, 1 H), 3.54 (bm) , 1 H), 3.24 (m, 1 H), 3.20-3.00 (m, 4 H), 2.64 (s, 3 H), 2.60 (m, 1 H), 2.54 (m, 1 H), 2.25 (s) , 1 H + 6 H), 2.08 (s, 3 H), 1.94 (m, 1 H), 1.74 (m, 1 H), 1.70-1.50 (m, 3 H), 1.40 (d, 3 H), 1 .30 (m, 1 H), 1 .30 (s, 3 H), 1 .26 (d, 3 H), 1 .17 (d, 3 H), 1.16 (d, 3 H) ), 1 .12 (d, 3 H), 0.86 (t, 3 H).

EXAMPLE 4 (11"521?, 5) -2'-Q-Acetyl-3-declaidinosyl-11, 12-d-deoxy-6-Q-methyl-3-oxo-12,11-oxycarbonyl- (benzhydrylideneamino) -methylene1-erythromycin A To a solution of intermediate 18 (1.5 g) and EDC (3.1 g) in DCM (100 mL) cooled to 0 ° C, DMSO (3.45 mL) was added under nitrogen atmosphere. After stirring at 0 ° C for 10 minutes, a solution of pyridinium trifluoroacetate (3.12 g) in anhydrous DCM (15 mL) was slowly added. After 10 minutes, the ice bath was removed. The reaction mixture was stirred for 3 hours at room temperature, and then quenched with water (150 mL) and extracted with DCM (3x250 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure.

The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (1-2 g). 1 H-NMR (CDCl 3) d: 7.80-7.20 (m, 10H), 6.40 (dd, 1H), 5.15 (s, 1H), 4.73 (m, 1H), 4.42 (d, 1H), 4.16 (d, 1H) ), 3.90 (q, 1H), 3.55 (m, 1H), 3.17 (m, 1H), 2.95 (m, 1H), 2.94 (d, 1H), 2.67 (m, 1H), 2.53 (s, 3 H) ), 2.43 (m, 1H), 2.33 (s, 6 H), 2.05 (s, 3 H), 2.00 (m, 1H), 1.74 (m, 1H), 1.65 (m, 1H), 1.53 (s, 3 H), 1.38 (d, 3 H), 1.23 (s, 3 H), 1.29 (d, 3 H), 1.25 (m, 1 H), 1.25 (d, 3 H), 1.14 (d, 3 H), 1.07 (d, 3H), 0.83 (t, 3 H). TLC: DCM \ MeOH 10 \ 1 (Rf = 0.30).

EXAMPLE 5 (11 «S21 ^) -3-Decladoinosyl-11,12-d-desox! -6-0-methy1-3-oxo-12,11-roxycarbonH-fbenzhydrylenoamino) -methylene1 ^ ritrornicin A A solution of Example 4 (0.030 g) in eOH (1 mL) was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.024 g). 1 H-NMR (CDCl 3) d: 7.80-7.20 (m, 10H), 6.38 (dd, 1H), 5.13 (s, 1H), 4.34 (d, 1H), 4.18 (d, 1H), 3.91 (q, 1H) ), 3.55 (m, 1H), 3.20 (m, 1H), 2.96 (m, 1H), 2.63 (s, 1H), 2.53 (s, 1H), 2.44 (m, 2H), 2.26 (s, 6 H) ), 2.00 (m, 1H), 1.70-1.45 (m, 7H), 1.45 (d, 1H), 1.30 (m, 4 H), 1.04 (d, 3 H), 0.96 (t, 3 H), 0.91 (d, 3 H).

TLC: DCMWIeOH 10 \ 1 (Rf = 0.34).

EXAMPLE 6 (11 £ 21 / S ^ '- O-Acetyl-S-DecladinosiM 1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amine) -methylene] -eritrom Cina A A solution of Example 4 (1.1 g) in acetonitrile (30 mL) and an aqueous solution of HCI at 1.2N (70 mL) was stirred at room temperature for 1 hour. After neutralizing the mixture with solid Na 2 CO 3 and evaporating the solvent, the aqueous phase was extracted with DCM (3 × 200 mL). The organic layer was dried over Na2SC > 4 and concentrated under reduced pressure to give the title compound (0.9 g). 1 H-NMR (CDCl 3) d: 5.45 (dd, 1 H), 4.75 (m, 1 H), 4.45 (d, 1 H), 4.40 (d, 1 H), 4.21 (d, 1 H), 3.82 (q, 1 H), 3.54 (m, 1 H), 3.09 (m, 1 H), 2.69 (m, 1 H), 2.68 (s, 3 H), 2.58 (m, 1 H), 2.41 (m , 1 H), 2.25 (s, 6 H), 2.07 (m, 3 H), 1 .95 (m, 1 H), 1.75 (m, 1 H), 1.60 (m, 1 H), 1.49 (s) , 3 H), 1.39 (d, 3 H), 1.35 (m, 1 H), 1.31 (s, 3 H), 1.26 (d, 3 H), 1.17 (d + d, 6 H), 1 .09 (d, 3 H), 0.88 (t, 3 H). TLC: DCMWleOH 10 \ 1 (Rf = 0.48).

EXAMPLE 7 (11 * 21 ¿) -2'-Q-Acetyl-3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11-roxycarbonyl- (amino) -methylene-erythromycin A To a solution of Example 6 (15.1 g) in anhydrous toluene (170 mL), benzaldehyde (2.52 mL) fresh distillate and pyridine (2.01 mL) were added, and the reaction mixture was refluxed for 4.5 hours. After evaporating the solvent, the residue was dissolved in acetonitrile (60 mL), and then an aqueous solution of HCI at 1.2N (120 mL) was added at room temperature. After stirring for 1.5 hours, the solvent was evaporated, and the aqueous acid solution was extracted with EtOAc (150 mL) and DCM (150 mL). The aqueous phase was neutralized with solid potassium carbonate and extracted with EtOAc (2x150 mL). The collected organic extracts were dried over Na 2 SO and concentrated under reduced pressure to give the title compound (11.5 g, 96% pure by NMR analysis). 1 H-NMR (CDCl 3) d: 5.45 (dd, 1 H), 4.75 (m, 1 H), 4.45 (d, 1 H), 4.40 (d, 1 H), 4.21 (d, 1 H), 3.82 ( q, 1 H), 3.54 (m, 1 H), 3.09 (m, 1 H), 2.69 (m, 1 H), 2.68 (s, 3 H), 2.58 (m, 1 H), 2.41 (m, 1 H), 2.25 (s, 6 H), 2.07 (m, 3 H), 1.95 (m, 1 H), 1.75 (m, 1 H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.35 (m, 1 H), 1.31 (s, 3 H), 1.26 (d, 3 H), 1 .17 (d + d, 6 H), 1.09 ( d, 3 H), 0.88 (t, 3 H).

EXAMPLE 8 (11 «¾21 ^) - 3-Decladoinosyl-11,12-diodeoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (amino) -methylene-1-erithromycin A A solution of Example 7 (0.012 g) in MeOH (1 mL) was stirred at room temperature overnight. After evaporating the solvent under reduced pressure, the crude material was purified by flash chromatography (eluting with: DCMWIeOH 100 \ 5), to give the title compound (0.007 g). 1 H-NMR (CDCl 3) d: 5.41 (dd, 1 H), 4.42 (d, 1 H), 4.33 (d, 1 H), 4.22 (d, 1 H), 3.83 (q, 1 H), 3.56 ( m, 1 H), 3.23 (d, 1H), 3.12 (m, 1 H), 3.02 (m, 1 H), 2.80 (d, 1 H), 2.69 (s, 3 H), 2.60 (m, 1 H), 2.54 (m, 1 H), 2.40 (d, 1 H), 2.33 (s, 6 H), 1.95 (m, 1 H), 1.9-1.50 (m, 3 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.35 (m, 1 H), 1.33 (s, 3 H), 1.32 (m, 1 H), 1.31 (d, 3 H), 1.26 (d, 3 H) , 1.16 (d, 3 H), 1.10 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 9 (1 OftSA 1 / -3-Decladinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonylmethylene-erythromycin A To a solution of intermediate 23 (0.050 g) in anhydrous DCM (25 mL), EDC (0.102 g) and DMSO (0.1 15 mL) were added under nitrogen atmosphere. The mixture was cooled to 0 ° C, and a solution of pyridinium trifluoroacetate (0.102 g) in DCM (0.5 mL) was added dropwise. The mixture was allowed to reach room temperature; After stirring for 5 hours, water (0 mL) was added, and the mixture was extracted with DCM (2x20 mL). The organic phase was dried over Na 2 SO 4, concentrated under reduced pressure, and the crude material was purified by preparative TLC (eluting with: DCMWIeOH 95 5). The recovered silica gel was stirred for 18 hours in MeOH (2 mL), the mixture was filtered, and evaporation of the solvent under reduced pressure gave the title compound (0.025 g). 1 H-NMR (CDCl 3) d: 4.90 (dd, 1 H), 4.32 (d, 1 H), 4.24 (d, 1 H), 3.85 (q, 1 H), 3.56 (m, 1 H), 3.32 (d. d, 1 H), 3.18 (m, 1 H), 3.12 (m, 1 H), 3.02 (m, 1 H), 2.80 (d, 1 H), 2.71 (dd, 1 H), 2.63 ( s, 3 H), 2.55 (m, 1 H), 2.47 (m, 1 H), 2.27 (s, 6 H), 1.87 (m, 1 H), 1.70 (m, 1 H), 1.62 (m, 1 H), 1.58 (m, 1 H), 1.50 (s, 3 H), 1.38 (d, 3 H), 1.30 (d, 3 H), 1.31 (s, 3 H), 1.30 (m, 1 H ), 1.25 (d, 3 H), 1.22 (m, 1 H), 1.14 (d, 3 H), 1 .07 (d, 3 H), 0.86 (t, 3 H).

EXAMPLE 10 (11"£ 21) -2'-Q-Acetyi-3-decladinosyl-11,1-d -deoxy-2-fluoro-6-methyl-3-oxo-12,11-roxycarbonyl- (amino) - methylenol-erythromycin A To a solution of Example 7 (0.284 g) in anhydrous THF (14 mL) cooled to -10 ° C, potassium tert-butoxide (1M in THF, 0.553 mL) was added under nitrogen. After 5 minutes, fluorobenzenesulfonimide (0.148 g) was added at -10 ° C. The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with DCM (15 mL) and washed with water (15 mL). The organic layer was dried over Na2SC and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH of 100 \ 0 \ 0, to 94 \ 6 \ 0.2), to give the title_composition (0.120 g). m \ z (ÍMH] +) = 687. 1 H-NMR (CDCl 3) d: 5.35 (dd, 1 H), 4.74 (M, 1 H), 4.48 (d, 1 H), 4.33 (d, 1 H), 3.96 (m, 1 H), 3.52 (m, 1 H), 2.89 (s, 3 H), 2.86 (m, 1 H), 2.72 (m, 1 H), 2.53 (m, 1 H); 2.27 (s, 6 H), 2.08 (s, 3 H), 2.0-1.94 (m, 2H), 1.82 (d, 3 H), 1.76 (m, 1 H), 1.64 (m, 1 H), 1.48 (d + m, 3 H + 1 H), 1.31 (s, 3 H), 1.26 (m, 6 H), 1.16 (d, 3 H), 1 .08 (d, 3 H), 0.92 (t, 3 H).

EXAMPLE 11 (11 £ 21) -3-Decladoinosyl-11,12-dideoxy-2-fluoro-6-Q-methyl-3-oxo-12,1-roxycarbonyl- (amino) -methylene-1-erythromycin A A solution of Example 10 (0.010 g) in MeOH (1 mL) was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.005 g). 1 H-NMR (CDCl 3) d: 5.33 (dd, 1 H), 4.42 (d, 1 H), 4.33 (d, 1 H), 4.03 (dd, 1 H), 3.53 (bm, 1 H), 3.18 (d. m, 1 H), 3.10 (m, 1 H), 2.93 (s, 3 H), 2.90 (m, 1 H), 2.54 (m, 2 H), 2.30 (s, 6 H), 2.09 (s, 1 H), 2.06 (m, 1 H), 1.96 (m, 1 H), 1.82 (d, 1 H), 1.62-1.50 (m, 6 H), 1.34 (s, 3 H), 1.27 (m, 4 H), 1.26 (s, 3 H), 1 .16 (d, 3 H), 1.08 (d, 3 H), 0.92 (t, 3 H).

EXAMPLE 12 (1 «¾21) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2 - (/ V-t-butylcarbamate) -ethylamino) -methylene -erythromycin A To a solution of Example 7 (1.34 g) in anhydrous acetonite (12 mL), tert -butyl (2-oxoethyl) carbamate (0.640 g) was added under nitrogen atmosphere, and the resulting mixture was stirred for 24 hours at room temperature. Sodium cyanoborohydride (1 M in THF, 2.0 mL) and acetic acid (0.114 mL) were added, and the reaction mixture was stirred for 12 hours at room temperature. After evaporating the solvent, the residue was dissolved in DCM (100 mL) and washed with saturated aqueous solution of NaHCO 3 (50 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was diluted in eOH (35 mL) and refluxed for 15 hours. The solvent was evaporated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: cyclohexane \ acetone 85 \ 15), to give the title compound (1.51 g, pure% by NMR analysis). m \ z (ÍMH] +) = 770.

EXAMPLE 13 { 11521 5) -2'-0-Acetyl-3-declaidinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl-2 - (amino) -ethylamino) -methienol -trict To a solution of Example 11 (1.5 g) in anhydrous DCM (5.4 mL), trifluoroacetic acid (0.6 mL) was added under a nitrogen atmosphere, and the resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was diluted with EtOAc (15 mL) and concentrated under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with saturated aqueous solution of NaHCC > 3 (50 mL), dried over Na2SC and concentrated under reduced pressure, to give the title compound (1.05 g). m \ z ([MH] +) = 670. 1 H-NMR (CDCl 3) d: 5.12 (dd, 1 H), 4.32 (d, 1 H), 4.21 (d, 1 H), 4.05 (m, 1 H ), 3.85 (q, 1 H), 3.58 (m, 1 H), 3.25 (dd, H), 3.20-3.0 (m, 4 H), 3.05 (m, 2H), 2.67 (m, 1 H), 2.68 (s, 3 H), 2.61 (m, 1 H), 2.40 (s, 6 H), 2.32 (m, 1 H), 1.91 (m, 1 H), 1.78-1.68 (m, 3 H) , 1.60 (m, 1 H), 1.47 (s, 3 H), 1.38 (d, 3 H), 1.32 (s, 3 H), 1.30 (d, 3 H), 1.29 (m, 1 H) , 1.27 (d, 3 H), 1.15 (d, 3 H), 1.11 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 14 (11 £ 21 / ¾-2'-0-Acetyl-3-declaidinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl-3-quinolineH-carbonylaminomethyl) -rnethenylene - erythromycin A To a solution of intermediate 25 (0.035 g) in anhydrous DCM (1.5 mL), EDC (0.041 g) and DMSO (0.041 mL) were added at 0 ° C under nitrogen atmosphere. After stirring at 0 ° C for 15 minutes, pyridinium trifluoroacetate (0.042 g) was added. The reaction mixture was stirred for 3 hours at room temperature, then quenched with water (3 mL) and extracted with DCM (5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by preparative TLC (eluting with; DCM \ MeOH 95 \ 5), to give the title compound (0.016 g). m \ z ([MH] +) = 838.

EXAMPLE 15 (11 «¾21 / a-3-Pec) adinosiI-11.12-d-Desoxy-6-Q-metH-3-oxo-12,11-foxycarbonyl- (3-qu8-N-halo-carbonylaminomethyl) -methylene-1-ritromycin A A solution of Example 14 (0.016 g) in MeOH (1.5 mL) was stirred for 24 hours, and then concentrated under reduced pressure, to give the title compound (0.009 g). 1 H-NMR (CDCl 3) d: 9.50 (d, 1 H), 8.79 (d, 1 H), 8.16 (d, 1 H), 7.94 (d, 1 H), 7.84 (t, NH), 7.81 (t , 1 H), 7.61 (t, 1 H), 4.90 (dd, 1 H), 4.27 (d, 1 H), 4.19 (d, 1 H), 4.01 (m, 2H), 3.84 (d, 1 H) ), 3.52 (m, 3 H), 3.14 (m, 3 H), 2.70 (m, 1 H), 2.53 (s, 3 H), 2.54 (m, 1 H), 2.43 (m, 1 H), 2.27 (s, 6 H), 1.95 (m, H), 1.84 (d, 1 H), 1.75 (m, 1 H), 1.64 (m, 1 H), 1.60 (m, 1 H), 1.56 (s) , 3 H), 1.38 (d, 3 H), 1.30 (d, 3 H), 1.26 (s, 3 H), 1.22 (m, 1 H), 1.22 (d, 3x3 H), 0.88 (t, 3 H).

EXAMPLE 16 (11 £ 21 / ¾-2'-Q-Acetyl-3-declaidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl-f4- (4- ( pyridin-3-yl) -rnidazoyl-1-yl) -butyridomethyl) -methyleneol-erythromycin A To a solution of intermediate 26 (0.040 g) in anhydrous DCM (3 mL), Dess-Martin periodinane (0.030 g) was added portionwise at room temperature within 5 hours. The reaction was quenched with a Na2S203 solution (5% in saturated aqueous solution of NaHCC > 3.2 mL), stirred for 1 hour, and then extracted with DCM (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMVMeOH 95 \ 5), to give the title compound (0.029 g). TLC: DCM \ MeOH 90 \ 10 (Rf = 0.42).

EXAMPLE 17 (11, 21 /¾-3- Decladinosil-11.12-didesoxy-6-Q-methyl-3 -oxo-12.11 -roxylcarbonyl- (4- (4-pyridin-3-yl) mi'dazol-1 -yl) -buti > amidometin-methylene] - erftromycin A A solution of example 16 (0.029 g) in MeOH (2 ml_) was stirred for 24 hours, and then concentrated under reduced pressure, to give the title compound (0.023 g). HR N (CDCl 3) d: 8.98 (d, 1 H), 8.40 (dd, 1 H), 8.10 (dd, 1 H), 7.61 (d, 1 H), 7.35 (d, 1 H), 7.29 (m 1 H), 6.48 (t, NH), 4.89 (dd, 1 H), 4.30 (d, 2H), 4.21 (d, 1 H), 4.01 (m, 1 H), 3.83 (q, 1 H) , 3.73 (m, 1 H), 3.55 (m, 1 H), 3.34 (m, 1 H), 3.19 (m, 1 H), 3.08 (m, 2H), 2.65 (s, 3 H), 2.58 ( m, 1 H), 2.47 (m, 1 H), 2.34 (m, 1 H), 2.28 (s, 6 H), 2.3-2.1 (m, 4 H), 1.91 (m, 1 H), 1.81 ( m, 1 H), 1.80-1.54 (m, 3 H), 1.51 (s, 3 H), 1.39 (d, 3 H), 1.35 (m, 1 H), 1.32 (s, 3 H), 1.30 ( d, 3 H), 1.25 (d, 3 H), 1.12 (d, 3 H), 1.15 (d, 3 H), 1.12 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 18 (11 S21 / ¾-2'-0-Acetyl-3-declaidinosyl-11 12,11-roxkarbonyl- (3- (4- (pyridin-3-yl) -imidazole-1-ii) -propionamidomethyl-methyleneol- erythromycin A To a solution of intermediate 27 (0.039 g) in anhydrous DC (3 mL) under a nitrogen atmosphere, Dess Martin periodium (0.030 g) was added portionwise at room temperature within 5 hours. The reaction was quenched with a Na2S203 solution (5% in saturated aqueous NaHCO3 solution, 7 mL), stirred for 1 hour, and then extracted with DCM (15 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMMeOH 95 \ 5), to give the title compound (0.026 g). TLC: DCMWleOH 90? 10 (Rf = 0.35).

EXAMPLE 19 (11 £ 21 / 3-3-Decf adínosií-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (4- (pyridin-3-yl) - imidazol-1-yl) -propionamidomethyl-D-methyleneol-erythromycin A A solution of Example 18 (0.024 g) in MeOH (1 mL) was stirred for 24 hours, and then concentrated under reduced pressure, to give the title compound (0.020 g). 1 H-NMR (CDCl 3) d: 8.99 (d, 1 H), 8.45 (dd, 1 H), 8.08 (dd, 1 H), 7.58 (d, 1 H), 7.35 (d, 1 H), 7.29 (m , 1 H), 6.67 (t, NH), 4.80 (dd, 1 H), 4.36 (m, 2H), 4.30 (d, 1 H), 4.19 (d, 1 H), 3.83 (m, 2H), 3.61 (m, 1 H), 3.55 (m, 1 H), 3.25 (m, 2H), 3.04 (m, 2H), 2.70 (m, 2H), 2.62 (s, 3 H), 2.58 (m, 2H) ), 2.33 (s, 6 H), 2.32 (d, 1 H), 1.85 (m, 1 H), 1.80 (m, 1 H), 1.70 (m, 2H), 1.56 (m, 1 H) , 1.48 (s, 3 H), 1.45 (d, 3 H), 1.33 (s, 3 H), 1.21 (d, 3 H), 1.35 (m, 1H), 1.18 (d, 3 H), 1.04 ( d, 3 H), 0.95 (t, 3 H), 0.91 (d, 3 H).

EXAMPLE 20 fll ^ l aS-Deciadinosi l ^ -didesoxy-eO-methyl-a-oxo-IZH-roxycarbonyl- (2- (4- (pyridin-3-yl) -imidazol-1-yl) -acetamidomethyne-methylene1- erythromycin A To a solution of intermediate 28 (0.018 g) in anhydrous DCM (0.5 mL) under a nitrogen atmosphere, Dess-Martin periodonodium (0.020 g) was added portionwise at room temperature within 5 hours. The reaction was quenched with a Na 2 S 2 O 3 solution (5% in saturated aqueous NaHCO 3 solution, 2 mL), stirred for 1 hour, and then extracted with DCM (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by preparative TLC (eluting with: DCM leOH 10Y1), and the recovered silica gel was stirred overnight in MeOH (1 mL). The mixture was filtered, and evaporation of the solvent under reduced pressure gave the title compound (0.009 g). 1 H-NMR (CDCl 3) d: 9.02 (d, 1H), 8.49 (m, 1H), 8.11 (m, 1H), 7.55 (d, 1H), 7.43 (d, 1H), 7.30 (m, 1H), 6.58 (t, NH), 4.89 (dd, 1H), 4.70 (dd, 2H), 4.29 (d, 1H), 4.20 (d, 1H), 3.83 (m, 2H), 3.69 (m, 1H), 3.51 (m, 1H), 3.29 (m, 1H), 3.17 (m, 1H), 3.04 (m, 2H), 2.60 (s, 3 H), 2.54 (m, 1H), 2.44 (m, 1H), 2.31 (m, 1H), 2.27 (s, 6 H), 1.91 (m, 1H), 1.80 (m, 1H), 1.68 (m, 2H), 1.60 (m, 1H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.29 (s, 3 H), 1.29 (d, 3 H), 1.22 (m, 1 H), 1.25 (d, 3 H), 1.12 (d, 3 H), 1.10 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 21 (11 £ 21> ^ -3-Dedadinosyl-11,12-dideoxy-6-0-methyl-3-oxo-2.11-roxycarbonyl- (1 - (pyrrolidin-2-one) -methyl) -methylene1- erythromycin A To a solution of intermediate 29 (0.020 g) in anhydrous DCM (2 mL) under nitrogen atmosphere, Dess-Martin periodinane (0.017 g) was added portionwise at room temperature within 1 hour. After stirring for 5 hours, the reaction was quenched with a solution of Na2S203 (5% in saturated aqueous solution of NaHCO3, 2 mL), stirred for 1 hour, and then extracted with DCM (3x5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMAMeOH from 100 \ 0 to 95 \ 5), to give a compound which was dissolved in MeOH (2 mL) and stirred at room temperature overnight. Evaporation of the solvent gave the title compound (0.010 g). H-NMR (CDCl 3) d: 4.39 (m, 1 H), 3.76 (m, 1 H), 3.52 (m, 1 H), 3.39 (m, 1 H), 3.15 (m, 1 H), 3.04 ( m, 1 H), 2.41 (m, 1 H), 2.36 (m, 1 H), 2.32 (m, 1 H), 2.10 (m, 1 H), 2.02 (m, 1 H), 1.12 (d, 3 H).

EXAMPLE 22 (11 ·, 21 ^ -3-? 60? 3 € ?? 05 ?? - 11,? 2- <?? 30 ?? - 6 -? - G ???? - 3- ??? - 12,11-Roxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) -acetamidomethymethylene-erythromycin A To a solution of intermediate 30 (0.068 g) in anhydrous DCM (5 mL), Dess-Martin periodonodium (0.064 g) was added under a nitrogen atmosphere. The mixture was stirred at room temperature for 6 hours. The reaction was quenched with a solution of Na2S203 (5% in saturated aqueous solution of NaHCO3, 5 mL), stirred for 30 minutes, and then extracted with DCM (3x4 mL). The organic phase was washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude material was dissolved in MeOH (5 mL) and stirred overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.053 g). 1 H-NMR (CDCl 3) d: 8.70 (s, 1 H), 8.05 (d, 1 H), 8.02 (d, 1 H), 7.71 (td, 1 H), 7.64 (td, 1 H), 7.59 ( bt, 1 H), 4.1 1 (d, 1 H), 4.03 (m, 1 H), 3.34 (bm, 1 H), 2.98 (m, 1 H), 1 .01 (d, 3 H).

EXAMPLE 23 (11 £ 21 / a-3-Decladoinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12.11-roxycarbonyl- (3- (quinoxalyn-2-ylsulfanyl) -propionamidomethyl) -rnetileno1- erythromycin A To a solution of intermediate 31 (0.035 g) in anhydrous DCM (2.5 mL), Dess-Martin periodonodium (0.033 g) was added under a nitrogen atmosphere. The mixture was stirred at room temperature for 18 hours. The reaction was quenched with a solution of Na2S203 (5% in saturated aqueous solution of NaHCO3, 2 mL), stirred for 30 minutes, and then extracted with DCM (3x4 mL). The organic phase was washed with brine (3 mL), dried over Na 2 SO 4 and concentrated under reduced pressure. The crude material was dissolved in anhydrous MeOH (2 mL) and stirred overnight. The solvent was evaporated under reduced pressure, and the crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 95 \ 5), to give the title compound (0.011 g). 1 H-NMR (CDCl 3) d: 8.50 (s, 1 H), 8.00 (d, 1 H), 7.98 (d, 1 H), 7.70 (t, 1 H), 7.61 (t, 1 H), 6.69 ( bt, 1 H), 3.83 (m, 1 H), 3.68 (m, 1 H), 3.64 (m, 1 H), 3.34 (m, 1 H), 3.06 (m, 1 H), 2.77 (m, 1 H), 2.34 (m, 1 H), 1.1 1 (d, 3 H).

EXAMPLE 24 (11 £ 21 / fl-3-Decladoinosyl-11,12-dideoxy-6-Q-methy [-3-oxo-12,11-foxycarbonyl (quinolin-1-methylmethylene) -amino-1-methyl) -methylene-1-ritromycin TO To a solution of intermediate 32 (0.100 g) in anhydrous DCM (4 mL), Dess Martin periodium (0.110 g) was added portionwise within 3 hours under nitrogen atmosphere. The mixture was stirred at room temperature for 3 hours. The reaction was quenched with a Na2S203 solution (5% in saturated aqueous solution of NaHCO3, 2 mL), stirred for 45 minutes, and then extracted with DCM (3x4 mL). The organic phase was washed with brine (3 mL), dried over Na 2 SO 4 and concentrated under reduced pressure. The crude material was purified by preparative TLC (eluting with: DCM \ MeOH 95 \ 5), the recovered silica gel was stirred for 18 hours in MeOH (5 mL), the mixture was filtered, and then the evaporation of the solvent under pressure reduced, gave the title compound (0.015 g). m \ z ([H] +) = 780.

EXAMPLE 25 (11, 21 > ¾-3-Decladinosll-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonii fquinolin-4-ylmethyl) -amino-1-methyl) -methylene-erythromycin TO To a solution of Example 24 (0.015 g) in anhydrous MeOH (6 mL), palladium (10% by weight on carbon powder, 0.005 g) was added, and the mixture was stirred under a hydrogen atmosphere (6 atmospheres) for 20 minutes. hours. Filtration through a pad of celite eluting with MeOH (20 mL) and purification by flash chromatography (eluting with DCMWleOH from 100 \ 0 to 95 \ 5) and by preparative TLC (eluting with: DCM \ MeOH \ NH4OH 87.5 \ 12.5 \ 0.5), gave the title compound (0.002 g). 1 H-NMR (CDCl 3) d: 8.87 (d, 1 H), 8.10 (d, 2 H), 7.61 (d, 1 H), 7.70 (m, 1 H), 7.57 (m, 1 H), 4.38 (d , 1 H), 4.26 (d, 1 H), 3.55 (m, H), 3.28 ÷ 3.00 (m, 2H).

EXAMPLE 26 (1152 / ?, J) -3-Decladinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-2,11- [oxycarbonyl- (3- (4- (pyridine- 3-yl) -imidazol-1-yl) -propionamido) -methylene-1-erythromycin A To a solution of Example 6 (0.020 g) in anhydrous DMF (2 mL) under a nitrogen atmosphere, intermediate 48 (0.009 g), HATU (0.013 g) and DIPEA (0.013 mL) were sequentially added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (15 mL) and washed with water (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give a compound which was dissolved in MeOH (1 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.009 g). 1 H-NMR (CDCl 3) d: 9.04 (d, 1H), 8.44 (dd, 1H), 8.13 (m, 1H), 7.61 (m, 1H), 7.41 (d, 1H), 6.73 (bd, 1H), 5.08 (dd, 1H), 4.94 (m, 1H), 4.45 (m, 1H), 4.26 (m, 1H), 4.25 (d, 1H), 4.08 (m, 3 H), 3.80 (q, 1H), 3.51 (m, 1H), 3.15 (m, 1H), 3.04 (m, 1H), 2.98 (m, 1H), 2.65 (m, 1H), 2.60 (m, 1H), 2.52 (m, 1H), 2.44 (m, 1H), 2.39 (s, 3 H), 2.34 (m, 1H), 2.26 (s, 6 H), 1.90 (m, 1H), 1.75 (m, 1H), 1.65-1.55 (m, 3 H), 1.48 (s, 3 H), 1.37 (d, 3 H), 1.27 (d, 3 H), 1.22 (d, 3 H), 1.25 (m, 1 H), 1.17 (s, 3 H), 1.16 (d, 3 H), 1.12 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 27 (11 S, 21 3-3-Adinosyl-11,12-dideoxy-6-Q-metH-3-oxo-12,11-roxycarbonyl- (4- (4- (pyridin-3-yl) - imidazol-1-yl) -butyramido) -methylene-nol-erythromycin A and EXAMPLE 28 (H ^ I ^ -S-Decladinosyl-II. Z-dideoxy-eO-metH-S-oxo-^. H -roxycarbonyl- (4- (4- (pyridin-3-yl) -imidazol-1-yl) -butramide) -methylene-erythromycin A To a solution of Example 6 (0.020 g) in anhydrous DMF (2 mL) under a nitrogen atmosphere, intermediate 49 (0.009 g), HATU (0.013 g) and DIPEA (0.013 mL) were added sequentially. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (15 mL) and washed with water (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5, 90 \ 10), and the isomers (21 and (21 SJ) were isolated Each isomer was dissolved in MeOH (1 mL), and it was stirred at room temperature overnight, evaporation of the solvent under reduced pressure gave the title compound 27 (0.003 g) and the title compound 28 (0.006 g). 1 H-NMR (CDCl 3) d (example 27): 8.98 (d, 1H), 8.89 (bd, 1H), 8.46 (d, 1H), 8.08 (d, 1H), 7.61 (d, 1H), 7.41 (d , 1H), 7.28 (m, 1H), 5.33 (dd, 1H), 5.22 (dd, 1H), 4.31 (d, 1H), 4.25 (d, 1H), 4.14 (m, 2H), 3.88 (q, 1H), 3.56 (m, 1H), 3.27 (m, 1H), 3.17 (dd, 1H), 3.06 (m, 1H), 2.99 (m, 1H), 2.66 (m, 1H), 2.57 (s, 3 H), 2.46 (m, 1H), 2.40 (m, 2H), 2.27 (s, 6 H), 2.21 (m, 2H), 1.86 (m, 1H), 1.84 (m, 1H), 1.70-1.50 ( m, 3 H), 1.54 (s, 3 H), 1.36 (d, 3 H), 1.33 (d, 3 H), 1.29 (s, 3 H), 1.25 (m, 1 H), 1.24 (d, 3 H), 1.17 (d, 3 H), 1.08 (d, 3 H), 0.90 (t, 3 H). 1 H-R N (CDCl 3) d (example 28): 9.02 (d, 1H), 8.46 (dd, 1H), 8.11 (m, 1H), 7.61 (m, 1H), 7.37 (d, 1H), 7.31 (m, 1H), 6.47 (bd, 1H), 5.26 (dd, 1H), 4.81 (bt, 1H), 4.29 (d, 1H), 4.13 (m, 3 H), 3.81 (q, 1H), 3.54 (m, 1H), 3.17 (m, 1H), 3.08-3.04 ( m, 2H), 2.53 (s, 3 H), 2.56 (m, 1H), 2.45 (m, 1H), 2.36 (m, 1H), 2.27 (s, 6 H), 2.17-2.13 (m, 4 H) ), 2.00 (m, 1H), 1.80 (m, 1H), 1.68 (m, 1H), 1.60 (m, 1H), 1.51 (s, 3 H), 1.40 (d, 3 H), 1.29 (s, 3 H), 1.30 (d, 3 H), 1.25 (m, 1H), 1.22 (d, 3 H), 1.19 (d, 3 H), 1.16 (d, 3 H), 0.91 (t, 3 H) .

EXAMPLE 29 (11 £ 21 and?, 5) -3-Pecladinosyl-11, 12-d-deoxy-6-Q-methyl-3-oxo-12,11-roxycarbon-K5- (4- (pyridine-3- il) -imSdazol-1 -yl) -pentylamido) -methylene-1-erythromycin A To a solution of Example 6 (0.100 g) in D F anhydrous (5 ml_) under nitrogen atmosphere, intermediate 50 (0.048 g), HATU (0.063 g) and DIPEA (0.061 mL) were added sequentially. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DC (30 mL) and washed with water (25 mL). The organic phase was dried over Na 2 SO and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMVMeOH 95 \ 5, 90 \ 10), to give a compound which was dissolved in MeOH (5 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.090 g). H-R N (CDCl 3) d: 8.98 (d, 1H), 8.45 (d, 1H), 8.09 (d, 1H), 7.55 (s, 1H), 7.34 (s, 1H), 7.29 (m, 1H), 6.45 (bd, 1H), 5.19 (d, 1H), 4.82 (m, 1H), 4.29 (d, 1H), 4.12 (d, 1H), 3.98 (m, 2H), 3.80 (q, 1H), 3.55 (m, 1H), 3.17 (m, 1H), 3.06 (m, 2H), 2.55 (s + m, 1H + 3 H), 2.45 (m, 1H), 2.35 (m, 1H), 2.27 (s, 6 H), 2.21 (m, 2H), 1.98 (m, 1H), 1.88 (m, 2H), 1.80 (m, 2H), 1.60-1.50 (m, 3 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.35 (m, 1H), 1.30 (d + s, 3H + 3 H), 1.23 ( d, 3 H), 1.16 (d, 3H + 3 H), 0.89 (t, 3 H).

EXAMPLE 30 f 11"£ 21 / a-2'-Q-Acetyl-3-declaidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxcarbonyl- (2- (4 - (pyridin-3-in-itn -dazol-1-yl) -acetamido) -methylene-nol-erythromycin A J. EXAMPLE 31 (1, 21 > -2'-Q-Acetyl-3-decladinosyl-11.12-didesoxy) -6-Q-methyl-3-oxo-12.11- foxycarbonyl- (2- (4- (pyridin-3-yl) -imidazol-1-yl) -acetamido) -methylene-1-erythromycin A To a solution of Example 6 (0.100 g) in anhydrous DMF (8 mL) under nitrogen atmosphere, a solution of intermediate 47 (0.040 g) in anhydrous DMF (2 mL), HATU (0.057 g) and DIPEA ( 0.060 mL). The mixture was stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (30 mL) and washed with water (2x10 mL). The aqueous phase was extracted again with DCM (20 mL). The organic layers were collected, dried over Na2SC > 4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM IeOH from 95 \ 5 to 92 \ 8), to give the title compound 30 (0.008 g) and the title compound 31 (0.021 g). TLC: DCMWIeOH 95 \ 5 (Rf (example 30) = 0.53). TLC: DCMWIeOH 95 \ 5 (Rf (example 31) = 0.47).

EXAMPLE 32 (11. £ 21 /?) - 3-DecidinosiM 1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (4- (pyridin-3-yl) ) -imidazol-1 -yl) -acetamido) -methylene-1-erythromycin A A solution of Example 30 (0.007 g) in MeOH (5 mL) was stirred at room temperature for 48 hours. After evaporating the solvent under reduced pressure, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 80 \ 20), to give the title compound (0.003 g). H-NMR (CDCl 3) d: 9.19 (d, 1 H), 8.98 (d, 1 H), 8.47 (dd, 1 H), 8.06 (d, 1 H), 7.70 (d, 1 H), 7.42 ( d, 1 H), 7.29 (m, 1 H), 5.24 (d, 1 H), 4.80 (dd, 1 H), 3.18 (m, 1 H), 2.94 (d, 1 H), 0.99 (d, 3 H).

EXAMPLE 33 I11 * 21) -3-Decladolesl-11,12-d-Desoxy-6-O-methyl-3-oxo-12,11- [oxycarbonyl- (2- (4- (pyridine- 3-yl) -imidazol-1-yl) -acetamido) -rnetylene -T- erythromycin A A solution of Example 31 (0.021 g) in MeOH (5 mL) was stirred at room temperature for 48 hours. After evaporating the solvent under reduced pressure, the crude material was purified by flash chromatography (eluting with: DC \ MeOH from 100? 0 to 80? 20), to give the title compound (0.006 g). H-NMR (CDCl 3) d: 8.99 (d, 1 H), 8.47 (d, 1 H), 8.09 (d, 1 H), 7.58 (s, 1 H), 7.41 (s, 1 H), 7.30 (d. m, 1 H), 6.73 (d, 1 H), 4.88 (dd, 1 H), 4.67 (s, 1 H), 3.08 (m, 1 H), 2.41 (d, 1 H), 1.16 (d, 3 H).

EXAMPLE 34 (11) -3-Decladinosyl-11,12-dideoxy-6-Q-metH-3-oxo-12,11-roxycarbonyl - ((quinolin-4-yl) carbonylamino) -methylene-erythromycin A To a solution of Example 6 (0.100 g) in anhydrous DMF (8 mL) under nitrogen atmosphere, a solution of quinoline-4-carboxylic acid (0.026 g) in anhydrous DMF (2 mL), HATU (0.057 g) was added. and DIPEA (0.060 mL). The mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DC (30 mL) and washed with saturated aqueous NaHCO3 solution (2x10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 94 \ 6). The obtained compound was dissolved in MeOH (10 mL) and stirred overnight. After evaporation of the solvent, purification by flash chromatography (eluting with: DCMWleOH 90 \ 10) gave the title compound (0.032 g). 1 H-NMR (CDCl 3) d: 8.96 (d, 1H), 8.45 (d, 1H), 8.13 (d, 1H), 7.76 (t, 1H), 7.65 (t, 1H), 7.52 (d, 1H), 7.02 (d, 1H), 5.08 (dd, 1H), 3.17 (m, 1H), 2.60 (m, 1H), 1.28 (d, 3 H).

EXAMPLE 35 (11 *, 21, S) -3-DecladonesH-11.12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (3- (qu! Nolin-4-yl) -propionamido) -methylenol-erythromycin A To a solution of Example 6 (0.100 g) in anhydrous DF (8 mL) under a nitrogen atmosphere, 3-quinolin-4-yl-propionic acid (0.030 g), HATU (0.057 g) and DIPEA (0.060 mL) were added sequentially. ). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (30 mL) and washed with water (25 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 94 \ 6), to give a compound which was dissolved in MeOH (2 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.022 g). 1 H-NMR (CDCl 3) d: 8.82 (d, 1H), 8.10 (d, 1H), 8.07 (d, 1H), 7.71 (t, 1H), 7.61 (t, 1H), 7.26 (d, 1H), 6.50 (bd, 1H), 5.14 (dd, 1H), 4.92 (dd, 1H), 4.28 (d, 1H), 4.12 (d, 1H), 3.80 (q, 1H), 3.54 (m, 1H), 3.46 (m, 2H), 3.16 (m, 1H), 3.08 (m, 1H), 3.04 (m, 1H), 2.60 (m, 2H), 2.49 (s, 3 H), 2.45 (m, 1H), 2.39 (m, 1 H), 2.26 (s, 6 H), 2.00 (m, 1 H), 1.80 (m, 2H), 1.72 (m, 1 H), 1.65 (m, 1H), 1.60 (m, 1 H), 1.50 (s, 3 H), 1.39 (d, 3 H), 1.29 (d, 3 H), 1.28 (s, 3 H), 1.25 (m, 1 H), 1.24 (d, 3 H) , 1.18 (d, 3 H), 1.14 (d, 3 H), 0.91 (t, 3 H).

EXAMPLE 36 (11. £ 21) -3-Decladoinosyl-11.12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (4- (quinolin-butyl) -butyramido) -methylene-erythromycin A To a solution of Example 6 (0.075 g) in anhydrous DMF (6 mL) under a nitrogen atmosphere, intermediate 60 (0.027 g), HATU (0.043 g) and DIPEA (0.047 mL) were added sequentially. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (20 mL) and washed with saturated aqueous NaHCO3 solution (15 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 97 \ 3 to 95 \ 5), to give a compound which was dissolved in MeOH (2 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.039 g). 1 H-NMR (CDCIs) d: 8.81 (d, 1 H), 8.1 1 (d, 1 H), 8.09 (d, 1 H), 7.69 (t, 1 H), 7.58 (t, 1 H), 7.26 (m, 1 H), 6.47 (bd, 1 H), 5.20 (dd, 1 H), 4.88 (dd, 1 H), 4.30 (d, 1 H), 4.13 (s, 1 H), 4.13 (m , 2H), 3.80 (q, 1 H), 3.53 (m, 1 H), 3.19-3.00 (m, 5 H), 2.54 (s, 3 H), 2.61 -2.41 (m, 3 H), 2.29 ( s + m, 2H + 6 H), 2.11 (m, 2H), 2.00 (m, 1 H), 1.80-1.60 (m, 7H), 1.39 (d, 3 H), 1.29 (s + d, 3 H + 3 H), 1.24 (m, 4 H), 1.18 (d, 3 H), 1.14 (d, 3 H), 0.91 (t, 3 H).

EXAMPLE 37 (11 *, 21 ^ -S-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-rox.} Carbonyl- (5-fquinolin "4-yl) -pentylamido ) -met! leno1-erithromycin A To a solution of Example 6 (0.100 g) in anhydrous DMF (6 mL) under a nitrogen atmosphere, intermediate 62 (0.027 g), HATU (0.057 g) and DIPEA (0.057 mL) were added sequentially. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (20 mL) and washed with water (15 mL). The organic phase was dried over a2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (using: DC WleOH 95 \ 5), to give a compound which was dissolved in MeOH (2 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.024 g). 1 H-NMR (CDCl 3) d: 8.81 (d, 1 H), 8.1 1 (d, 1 H), 8.04 (m, 1 H), 7.70 (m, 1 H), 7.58 (m, 1 H), 7.27 (m, 1 H), 6.42 (bd, 1 H), 5.18 (dd, 1 H), 4.85 (dd, 1 H), 4.30 (m, 1 H), 4.13 (m, 1 H), 3.79 ( q, 1 H), 3.54 (m, 1 H), 3.17 (m, 1 H), 3.08 (m, 4 H), 2.58 (m, 1 H), 2.55 (s, 3 H), 2.45 (m, 1 H), 2.40 (m, 1 H), 2.27 (s, 6 H), 2.23 (m, 2 H), 1.98 (m, 1 H), 1.81 (m, 4 H), 1.75 (m , 1 H), 1.70 (m, 1 H), 1.65 (m, 1 H), 1.60 (m, 1 H), 1.50 (s, 3 H), 1.40 (d, 3 H), 1.30 (d, 3 H), 1.28 (s, 3 H), 1 .24 (d, 3 H), 1.20 (m, 1 H), 1.18 (d, 3 H), 1.14 (d, 3 H), 0.89 (t, 3 H).

EXAMPLE 38 (11 S, 21 / ?, .fl-3-DecidinosiM 1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxcarbon ^ 1- (3- (4-phenyl) ^ m ^ dazol- - ^ l) - ropionarndo) -meti ^ eno ^ - erythromycin A To a solution of Example 7 (0.050 g) in anhydrous DMF (4 mL) under nitrogen atmosphere, a solution of intermediate 65 (0.018 g) in anhydrous DMF (1 mL), HATU (0.013 g) and DIPEA ( 0.013 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (15 mL) and washed with saturated aqueous solution of NaHCO 3 (10 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 94 \ 6), to give a compound which was dissolved in MeOH (2 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.031 g). 1 H-NMR (CDCl 3) d: 7.78 (d, 2 H), 7.47 (d, 1 H), 7.31 (t, 2 H), 7.27 (d, 1 H), 7.16 (t, 1 H), 6.64 (d, 1 H), 5.04 (dd, 1 H), 4.99 (m, 1 H), 4.20 (m, 1 H), 3.01 (m, 1 H), 2.60-2.50 (m, 2H), 2.33 (dd, 1 H), 1.12 (d, 3 H).

EXAMPLE 39 f11 ^ 21 P, 5) -3-DecIadinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl-f2- (4-phenylHmidazol-1) ) -acetamido) -metHeno1 ^ ritromycin A To a suspension of intermediate 67 (0.022 g) in DMF anhydrous (1.6 mL), HATU (0.037 g) and DIPEA (0.015 mL) were added sequentially. The mixture was stirred under a nitrogen atmosphere for 30 minutes, and then Example 7 (0.050 g) was added. After stirring at room temperature overnight, the reaction mixture was diluted with DCM (3.5 mL), washed with an aqueous solution of 5% NaHCO3 (3 mL) while cooling on ice, and the aqueous phase was extracted with DCM (2.5 mL). The collected organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (10 mL) and stirred at room temperature overnight. After evaporation of the solvent under reduced pressure, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH from 100 \ 0 \ 0 to 94 \ 6 \ 0.5), to give the title compound ( 0.010 g). 1 H-NMR (DMSO) d: 8.62 (d, 1 H), 7.71 (d, 2 H), 7.58 (d, 1 H), 7.49 (d, 1 H), 7.33 (t, 2 H), 7.17 (t , 1 H), 4.69 (d, 1 H), 4.62 (d, 1 H), 4.59 (d, 1 H), 3.19 (m, 1 H), 2.59 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 40 (11 £ ._? /?, 5) -3-Decladinosil-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-rox} carbonyl- (3- (4-thiophen-2-yl-imidazol-1-yl) -proponamido) -methyl ene-erythromycin A To a solution of Example 7 (0.034 g) in anhydrous DMF (4 mL) under nitrogen atmosphere, a solution of intermediate 69 (0.012 g) in anhydrous DMF (1 mL), HATU (0.019 g) and DIPEA ( 0.020 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, the residue was dissolved in DCM (10 mL), and washed with saturated aqueous solution of NaHCC > 3 (5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM vleOH from 100 \ 0 to 94 \ 6), to give a compound which was dissolved in MeOH (5 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.020 g). 1 H-NMR (CDCl 3) d: 7.46 (d, 1 H), 7.31 (dd, 1 H), 7.20 (d, 1 H), 7.14 (dd, 1 H), 7.00 (dd, 1 H), 6.68 (d. d, 1 H), 5.08 (dd, 1 H), 4.40 (m, 1 H), 4.20 (m, 1 H), 3.05 (m, 1 H), 2.68 (m, 1 H), 2.50 (m, 1 H), 2.38 (dd, 1 H), 1.16 (d, 3 H).

EXAMPLE 41 (11 £ 21?, 5) -3-Decladoinosii-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (3-f3- (1,3-thiazole-2) -yl) -1 H-pyrazol-1 -yl] propionamido) -methylene'l-erythromycin A To a solution of Example 7 (0.050 g) in anhydrous DMF (4 mL) under nitrogen atmosphere, a solution of intermediate 70 (0.017 g) in anhydrous DMF (1 mL), HATU (0.029 g) and DIPEA ( 0.030 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (0 mL) and washed with saturated aqueous solution of NaHCC > 3 (5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 95 \ 5), to give a compound which was dissolved in MeOH (3 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure and purification by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 95 \ 5) gave the title compound (0.007 g). m \ z ([MH] +) = 832.

EXAMPLE 42 (11"£ 21 y ?,) -2'-Q-Acetyl-3-declaidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2" S - / g '-butoxycarbonylamino-3- (1 y -indol-3-yl) -propionamido) -methylene-erythromycin A To a solution of Example 6 (0.050 g) in anhydrous DMF (4 mL) under a nitrogen atmosphere, (2¿) - / er-butoxycarbonylamino-S-1-indol-Si-propionic acid (0.027 g) was added sequentially, HATU (0.031 g) and DIPEA (0.031 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (10 mL) and washed with saturated aqueous solution of NaHCO 3 (5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM vIeOH from 98 \ 2 to 97 \ 3), to give the title compound (0.043 g). m z ([H] +) = 955.

EXAMPLE 43 11, 21 / ?, 5) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl-2 (2-S) -fethoxycarbonylamino -3- (1 > ^ idol-3-H propionamido) -methylene-1-erithromycin A A solution of Example 42 (0.013 g) in MeOH (2 mL) was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.010 g). m \ z ([MH] +) = 913.

EXAMPLE 44 (11, 21) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxcarbonyl- ((25) -2-aminO "3- (1 i ^ 8ndol-3-yl) -propionamido) -methyl-ene-erythromycin A To a solution of Example 42 (0.025 g) in anhydrous DCM (0.5 mL) cooled to 0 ° C, trifluoroacetic acid (0.1 mL) was added. After removing the ice bath, the reaction mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 mL). The aqueous phase was extracted with DCM (3x3 mL). The collected organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMMvleOH 97 \ 3), to give a compound that was dissolved in MeOH (1 mL), and the solution was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.004 g). 1 H-NMR (CDCl 3) d: 8.12 (bs, 1 H), 8.06 (d, 1 H), 7.65 (d, 1 H), 7.36 (d, 1 H), 7.19 (t, 1 H), 7.16 ( d, 1 H), 7.13 (t, 1 H), 5.35 (dd, 1 H), 4.75 (dd, 1 H), 3.70 (dd, 1 H), 3.34 (dd, 1 H), 3.09- 3.04 (m, 3 H), 2.46-2.44 (m, 2H), 1.20 (d, 3 H). m \ z ([MH] +) = 813.

EXAMPLE 45 (11. £ 21 / ?, ¾-3-Decladoinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl) - (2-f-kinoxatin-2-ylsulfanil) ) -acetamfdo) -methylene1-erythromycin A To a solution of (quinoxalin-2-ylsulfanyl) -acetic acid (0.095 g) in anhydrous DMF (8.3 mL) under a nitrogen atmosphere, HATU (0.164 g) and DIPEA (0.089 mL) were added. The reaction mixture was stirred at room temperature for 30 minutes, and then Example 6 (0.262 g) was added. The reaction mixture was stirred at room temperature for 20 hours, and then diluted with DCM (30 mL) and washed with an aqueous solution of 5% NaHCO 3 (20 mL). The aqueous phase was extracted with DCM (25 mL), and the collected organic layers were washed with an aqueous solution of 5% NaHCO 3 (20 mL), dried over Na 2 SO 4 and concentrated under reduced pressure. The residue was dissolved in eOH (10 mL), and stirred at room temperature overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DC \ MeOH \ NH4OH from 100 \ 0 to 93 \ 7 \ 1), to give the title compound (0.199 g). 1 H-NMR (CDCl 3) d: 8.67 (s, 1 H), 8.19 (dd, 1 H), 8.04 (dd, 1 H), 7.90 (d, 1 H), 7.74 (dt, 1 H), 7.66 ( dt, 1 H), 5.20 (dd, 1 H), 4.67 (d, 1 H), 4.30 (d, 1 H), 4.06 (m + d, 1 H + 1 H), 3.95 (d, 1 H) , 3.73 (q, 1 H), 3.52 (m, 2H), 3.16 (dd, 1 H), 3.06-3.0 (m, 2H), 2.52 (s, 3 H), 2.50-2.40 (m, 2H), 2.42 (dd, 1 H), 2.27 (s, 6 H), 1.92 (m, 1 H), 1.81-1.65 (m, 2H), 1.66 (m, 1 H), 1.51 (m, 1 H), 1.47 (s, 3 H), 1.36 (d, 3 H), 1 .27 (d, 3 H), 1.24 (m, 1 H), 1.24 (d, 3 H), 1.23 (s, 3 H), 1.12 (d, 3 H), 1.06 (d, 3 H), 0.81 (t, 3 H).

EXAMPLE 46 (11 £ 21) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-2,11-hydroxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) -acetamide ) -methylene1-erythromycin A To a solution of (quinoxalin-2-ylsulfanyl) -acetic acid (0.395 g) in anhydrous DMF (5 mL) under nitrogen atmosphere, HATU (0.682 g) and DIPEA (0.365 mL) were added at room temperature. The reaction mixture was stirred at room temperature for 30 minutes, and then a solution of example 7 (1.0 g) in anhydrous DMF (3 mL) was added. The reaction mixture was stirred at room temperature for 3 hours, then poured into an aqueous solution of 5% NaHC03 (30 mL), and the solution was extracted with Et20 (2x30 mL). The collected organic layers were washed with brine (30 mL), dried over Na 2 SO 4 and concentrated under reduced pressure. The residue was dissolved in MeOH (25 mL) and stirred at room temperature overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH from 100 \ 0 \ 0 to 93 ± 0.2). Crystallization from EtOAc gave the title compound (0.454 g, isomer (21 S) 99% pure by NMR analysis). H-NMR (CDCl 3) d: 8.67 (s, 1 H), 8.19 (dd, 1 H), 8.04 (dd, 1 H), 7.90 (d, 1 H), 7.74 (dt, 1 H), 7.66 ( dt, 1 H), 5.20 (dd, 1 H), 4.67 (d, 1 H), 4.30 (d, 1 H), 4.06 (m + d, 1 H + 1 H), 3.95 (d, 1 H) , 3.73 (q, 1 H), 3.52 (m, 2H), 3.16 (dd, H), 3.06-3.0 (m, 2H), 2.52 (s, 3 H), 2.50-2.40 (m, 2H), 2.42 (dd, 1 H), 2.27 (s, 6 H), 1.92 (m, 1 H), 1.81-1.65 (m, 2H), 1.66 (m, 1 H), 1.51 (m, 1 H), 1.47 ( s, 3 H), 1 .36 (d, 3 H), 1 .27 (d, 3 H), 1 .24 (m, 1 H), 1.24 (d, 3 H), 1.23 (s, 3 H) ), 1.12 (d, 3 H), 1.06 (d, 3 H), 0.81 (t, 3 H).

EXAMPLE 47 (11 £ 21 >?,. A-3-DecladinosiM 1, 2-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl-f (4- (2,3-dihydro-benzof1 , 41-dioxin-6-yl) -4-oxo) -butyramide) - methyleneol-erythromycin A To a solution of 4- (2,3-dihydro-benzo [1,4] dioxin-6-yl) 4-oxo-butyric acid (0.1165 g) in anhydrous DMF (9.5 mL) under nitrogen atmosphere, HATU was added (0.188 g) and DIPEA (0.102 mL). The reaction mixture was stirred at room temperature for 30 minutes, and then Example 7 (0.300 g) was added. The reaction mixture was stirred at room temperature for 20 hours, and then diluted with DCM (30 mL) and washed with an aqueous solution of 5% NaHCO 3 (20 mL). The aqueous phase was extracted with DCM (25 mL)The organic layers collected were washed with an aqueous solution of 5% NaHC03 (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was dissolved in MeOH (10 mL), and stirred at room temperature overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH from 100 \ 0 \ 0 to 93 \ 7 \ 1), to give the title compound (0.170 g). 1 H-NMR (CDCl 3) d: 7.52 (d, 2 H), 6.89 (d, 1 H), 6.73 (d, NH), 5.20 (dd, 1 H), 4.84 (dd, 1 H), 4.35-4.25 (m, 5 H), 4.13 (d, 1 H), 3.80 (q, 1 H), 3.60-3.55 (m, 2H), 3.32-3.22 (m, 2H), 3.18 (dd, 1 H), 3.10-3.00 (m, 2H), 2.65-2.55 (m, 2H), 2.60 (s, 3 H), 2.44 (m, 2H), 2.27 (s, 6 H), 2.27 (m, 1 H), 1.99 (m, 1 H), 1.80 (dd, 1 H), 1.75 (m, 1 H), 1.68 (m, 1 H), 1 .60 (m, 1 H), 1.50 (s, 3 H), 1 .40 (d, 3 H), 1.32 (s, 3 H), 1 .30 (d, 3 H), 1 .25 ( m, 1 H), 1.24 (d, 3 H), 1.19 (d, 3 H), 1.17 (d, 3 H), 0.93 (t, 3 H).

EXAMPLE 48 (11. £ 21?,) -3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl-f4- (4-oxo-4,5,6, 7-1-tetrahydro-benzof> fltiofen-2-yl) -4-oxo-butyramido) -methylene-1-erythromycin A To a solution of 4- (4-oxo-4,5,6,7-tetrahydro-benzo [>] tofen-2-yl) -4-oxo-butyric acid (0.013 g) in anhydrous DMF (0.850) mL) under a nitrogen atmosphere, HATU (0.019 g) and DIPEA (0.010 mL) were added. The reaction mixture was stirred at room temperature for 30 minutes, and then Example 6 (0.028 g) was added. The reaction mixture was stirred at room temperature for 2.5 hours, then diluted with DCM (2 mL) and washed with an aqueous solution of 5% NaHCO 3 (2 mL). The aqueous phase was extracted with DCM (1.5 mL), the collected organic layers were dried over Na2SO4, and concentrated under reduced pressure. The residue was dissolved in MeOH (5 mL) and stirred at room temperature for 24 hours. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH from 100 \ 0 \ 0 to 92 \ 8 \ 0.2), to give the title compound (0.031 g). 1 H-RN (CDCl 3) d: 8.02 (s, 1 H), 6.68 (d, NH), 5.13 (dd, 1 H), 4.88 (dd, 1 H), 4.32 (d, 1 H), 4.14 (d , 1 H), 3.81 (q, 1 H), 3.55 (m, 1 H), 3.28 (m, 2 H), 3.21 (m, 1 H), 3.09-3.03 (m, 4 H), 2.62 (s, 3 H), 2.63-2.57 (m, 6 H), 2.46 (dd, 1H), 2.35 (s, 6 H), 2.24 (m, 2H), 1.98 (m, 1 H), 1.80-1.70 (m, 3 H), 1.60 (m, 1H), 1.49 (s, 3 H), 1.40 (d, 3 H), 1.32 (s, 3 H), 1.29 (d, 3 H), 1 .25 (m, 4 H), 1.18 (d, 3 H), 1.17 (d, 3 H), 0.92 (t, 3 H).

EXAMPLE 49 (11"!, 21 ^ -S-Decladinosyl-thia-dideoxy-SO-methyl-S-oxo- ^. H- roxycarbonif- (4- (4-oxo-4,5,6,7-tetrahydro -benzof / ¾thiophen-2-yl) -4-oxo-butyramido) -metholene-erythromycin A To a solution of 4- (4-oxo-4,5,6,7-tetrahydro-benzo [] thiophen-2-yl) -4-oxo-butyric acid (1280 g) in anhydrous DMF (12 ml_) under an atmosphere of nitrogen, HATU (2.02 g) and DIPEA (1.06 mL) were added. The reaction mixture was stirred at room temperature for 30 minutes, and then a solution of example 7 (2.90 g) in anhydrous DMF (10 mL) was added. The reaction mixture was stirred at room temperature overnight, then diluted with EtOAc (100 mL) and washed with an aqueous solution of 5% NaHCO 3 (2x50 mL) and brine (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 98 \ 2), to give a compound which was dissolved in MeOH (150 mL) and stirred overnight. After evaporating the solvent, the residue was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 97 \ 3), to give the title compound (2.40 g, 95% pure isomer (21 S) by NMR). 1 H-NMR (CDCl 3) d: 8.02 (s, 1 H), 6.68 (d, NH), 5.13 (dd, 1 H), 4.88 (dd, 1 H), 4.32 (d, 1 H), 4.14 (d, 1 H), 3.81 (q, 1 H), 3.55 (m, 1 H), 3.28 (m, 2 H), 3.21 (m, 1 H), 3.09-3.03 (m, 4 H), 2.62 (s, 3 H), 2.63-2.57 (m, 6 H), 2.46 (dd, 1 H), 2.35 (s, 6 H), 2.24 ( m, 2H), 1.98 (m, 1 H), 1.80-1.70 (m, 3 H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1.40 (d, 3 H), 1.32 (s, 3 H), 1.29 (d, 3 H), 1 .25 (m, 4 H), 1.18 (d, 3 H), 1.17 (d, 3 H), 0.92 (t, 3 H).

EXAMPLE 50 (11 > 21y?, ^) - 3-Decladinosi > -11,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (4-f4-methoxy-3-nitro-phenyl) -4-oxo-butyramido) -methylene-T-erythromycin TO To a solution of 4- (4-methoxy-3-nitro-phenyl) -4-oxo-butyric acid (0.136 g) in anhydrous DMF (9 mL) under nitrogen atmosphere, HATU (0.205 g) and DIPEA (0.1 10 mL) were added. The reaction mixture was stirred at room temperature for 30 minutes, and then Example 6 (0.300 g) was added. The reaction mixture was stirred at room temperature for 2.5 hours, then diluted with DCM (21 mL) and washed with an aqueous solution of 5% NaHCOs (18 mL). The aqueous phase was extracted with DCM (15 mL), the collected organic layers were dried over Na2SO4, and concentrated under reduced pressure. The residue was dissolved in MeOH (30 mL) and DCM (2 mL) and stirred at room temperature for 48 hours. After evaporating the solvent, the crude material was purified by LC (mobile phase: A \ B 85 \ 15 for 1 minute, from 85 \ 15 to 15 \ 85 in 20 minutes; ? = 255 nm), to give the title compound (0.149 g). 1 H-NMR (CDCl 3) d: 8.47 (d, 1 H), 8.19 (dd, 1 H), 7.15 (d, 1 H), 6.69 (d, NH), 5.18 (dd, 1 H), 4.85 (dd) , 1 H), 4.31 (d, 1 H), 4.14 (d, 1 H), 4.04 (s, 3 H), 3.80 (q, 1 H), 3.54 (m, 1 H), 3.32 (m, 2 H) , 3.18 (dd, 1 H), 3.06-3.0 (m, 2H), 2.66 (m, 2H), 2.60 (s, 3 H), 2.46 (m, 1 H), 2.42 (dd, 1 H), 2.28 (s, 6 H), 1.98 (m, 1 H), 1.81-1.55 (m, 4 H), 1.49 (s, 3 H), 1.40 (d, 3 H), 1.32 (s, 3 H), 1.30 (d, 3 H), 1.25 (d, 3 H), 1.25 (m, 1 H), 1.18 (d, 3 H), 1.17 (d, 3 H), 0.81 (t, 3 H).

EXAMPLE 51 (11 £ 21) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (4- (4-methoxy-3-nitro-phenyl) -4 -oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (4-methoxy-3-nitro-phenyl) -4-oxo-butyric acid (2782 g) in anhydrous DMF (36 mL) under nitrogen atmosphere, HATU (1230 g) and DIPEA ( 0.656 mL). The reaction mixture was stirred at room temperature for 30 minutes, and then Example 7 (1.8 g) was added. The reaction mixture was stirred at room temperature for 3 hours, then diluted with Et20 (200 mL) and washed with an aqueous solution of 5% NaHCO3 (2x100 mL). The aqueous phase was extracted with Et20 (50 mL) and DCM (50 mL), and the combined organic layers were dried over Na2SO and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ eOH from 100? 0 to 96 \ 4). The obtained compound was dissolved in MeOH (100 mL) and stirred at room temperature overnight. After evaporating the solvent, the product was purified by flash chromatography (eluting with: DCMMVleOH from 100 \ 0 to 96 \ 4), to give the title compound (1510 g, 95% pure (21 5) isomer by analysis of NMR). H-NMR (CDCl 3) d: 8.47 (d, 1 H), 8.19 (dd, 1 H), 7.15 (d, 1 H), 6.69 (d, NH), 5.18 (dd, 1 H), 4.85 (dd) , 1 H), 4.31 (d, 1 H), 4.14 (d, 1 H), 4.04 (s, -OCH3), 3.80 (q, 1 H), 3.54 (m, 1 H), 3.32 (m, 2H ), 3.18 (dd, 1 H), 3.06-3.0 (m, 2H), 2.66 (m, 2H), 2.60 (s, 3 H), 2.46 (m, 1 H), 2.42 (dd, 1 H), 2.28 (s, 6 H), 1.98 (m, 1 H), 1.881-1.55 (m, 4 H), 1.49 (s, 3 H), 1.40 (d, 3 H), 1.32 (s, 3 H) ), 1.30 (d, 3 H), 1.25 (d, 3 H), 1.25 (m, 1 H), 1.18 (d, 3 H), 1.17 (d, 3 H), 0.81 (t, 3 H).

EXAMPLE 52 (11 £ 21 / ?,.S) 3-Decladinosyl-11, 12-dideoxy-6-Q-methylene-3-oxo-12,11-hydroxycarbonyl- (4-f2 ^ idroxy ^ , 5-dimethoxy-phenol) ^ - oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (2-hydroxy-4,5-dimethoxy-phenyl) -4-oxo-butyric acid (0.137 g) in anhydrous DMF (9 mL) under nitrogen atmosphere, HATU (0.205 g) was added. g) and DIPEA (0.1 10 mL). The reaction mixture was stirred at room temperature for 30 minutes, and then Example 6 (0.300 g) was added. The reaction mixture was stirred at room temperature for 2.5 hours, then diluted with DCM (21 mL) and washed with an aqueous solution of 5% NaHCO3 (18 mL). The aqueous phase was extracted with DCM (15 mL), and the combined organic layers were dried over Na 2 SO and evaporated under reduced pressure. The residue was dissolved in MeOH (0 mL) and stirred at room temperature for 24 hours. After evaporating the solvent, the crude material was purified by LC (mobile phase: A \ E3 from 85 \ 15 to 15 \ 85 in 20 minutes;? = 237 nm), to give the title compound (0.120 g). 1 H-NMR (CDCl 3) d: 12.49 (s, 1 H), 7.14 (s, 1 H), 6.71 (d, NH), 6.44 (s, 1 H), 5.18 (dd, 1 H), 4.88 ( dd, 1 H), 4.31 (d, 1 H), 4.14 (d, 1 H), 3.91 (s, 3 H), 3.88 (s, 3 H), 3.80 (q, 1 H), 3.55 (m, 1 H), 3.41-3.30 (m, 2H), 3.20 (dd, 1 H), 3.1 1-3.0 (m, 2H), 2.70-2.60 (m, 2H), 2.61 (s, 3 H), 2.52 ( m, H), 2.43 (dd, 1 H), .31 (s, 6 H), 1 .98-1.70 (m, 3 H), 1.60 (m, 1 H), 1.50 (s, 3 H) ), 1.30 (d, 3 H), 1.26 (d, 3 H), 1.25 (m, 1 H), 1.24 (d + d, 6 H), 1.19 (d, 3 H), 1.17 (d, 3 H) ), 0.91 (t, 3 H).

EXAMPLE 53 (? ^??, ^^ - ????????? ß ?? -?,? S - ???? ßß ??? - ß -? - ?????? ^ - ??? -? S, ?? - roxicarbonjI-f4- (3-h8droxi ^ -methoxy-phen¡l) ^ - oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (3-hydroxy-4-methoxy-phenyl) -4-oxo-butyric acid (0.121 g) in anhydrous DMF (9 mL) under nitrogen atmosphere, HATU (0.205 g) and DIPEA ( 0.1 10 mL). The reaction mixture was stirred at room temperature for 30 minutes, and then Example 6 (0.300 g) was added. The reaction mixture was stirred at room temperature for 2.5 hours, then diluted with DCM (21 mL) and washed with an aqueous solution of 5% NaHCO 3 (18 mL). The aqueous phase was extracted with DCM (15 mL), and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (30 mL) and DCM (2 mL) and stirred at room temperature for 48 hours. After evaporating the solvent, the crude material was purified by LC (mobile phase: A \ B 85 \ 15 for 1 minute, from 85 \ 15 to 15 \ 85 in 20 min.; ? = 230 nm), to give the title compound (0.020 g). H-NMR (CDCl 3) d: 7.57 (m, 2H), 6.89 (d, 1 H), 6.71 (d, 1 H), 5.88 (bs, 1 H), 5.22 (dd, 1 H), 4.81 (dd) , 1 H), 4.31 (d, 1 H), 4.13 (d, 1 H), 3.96 (s, 3 H), 3.81 (q, 1 H), 3.55 (m, 1 H), 3.31 (m, 2H ), 3.22 (m, 1 H), 3.09-3.04 (m, 2H), 2.66-2.54 (m, 4 H), 2.61 (s, 3 H), 2.44 (dd, 1 H), 2.34 (s, 6) H), 2.00 (m, H), 1.81 -1.70 (m, 3 H), 1.6 (m, 1 H), 1.50 (s, 3 H), 1.41 (d, 3 H), 1.31 (s, 3 H), 1.29 (d, 3 H), 1.25 (d, 3 H), 1.25 (m, 1 H), 1.19 (d, 3 H), 1.17 (d, 3 H), 0.93 ( t, 3 H).

EXAMPLE 54 (1 £ 21 «fl-3-DecladinosiH 1, 12-dideoxy-6-Q-methyl-3-oxo-2,11-roxycarbonyl- (4- (3-hydroxy-4-rnetoxy-phen L) -4-oxo-butyramido) -methylene] - erythromycin A To a solution of 4- (3-hydroxy-4-methoxy-phenyl) -4-oxo-butyric acid (0.273 g) in anhydrous DMF (3.5 mL), HOBT (0.165 g) and EDC ( 0.234 g). After stirring for 5 minutes, Example 7 (0.627 g) was added, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with DCM (15 mL) and washed with an aqueous solution of 5% NaHCO 3 (10 mL). The organic layer was washed with brine (10 mL), dried over Na 2 SO 4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 97 \ 3 to 95 \ 5), to give a compound which was dissolved in MeOH (10 mL) and stirred at room temperature overnight. After evaporation of the solvent, the compound was purified by preparative LC (Waters XTerra MS C18 column (19 x 300 mm, 7 pm); flow rate - 12 mL \ min, A \ B from 70 \ 30 to 10 \ 90 in 25 minutes;? = 230 nm), to give the title compound (0.165 g, isomer (21) 94% pure by NMR analysis). 1 H-NMR (CDCl 3) d: 7.57 (m, 2 H), 6.89 (d, 1 H), 6.71 (d, 1 H), 5.88 (bs, 1 H), 5.22 (dd, 1 H), 4.81 (dd) , 1 H), 4.31 (d, 1 H), 4.13 (d, 1 H), 3.96 (s, 3 H), 3.81 (q, 1 H), 3.55 (m, 1 H), 3.31 (m, 2H ), 3.22 (m, 1 H), 3.09-3.04 (m, 2H), 2.66-2.54 (m, 4 H), 2.61 (s, 3 H), 2.44 (dd, 1 H), 2.34 (s, 6) H), 2.00 (m, 1 H), 1.81-1.70 (m, 3 H), 1.6 (m, 1 H), 1.50 (s, 3 H), 1 .41 (d, 3 H) , 1 .31 (s, 3 H), 1.29 (d, 3 H), 1 .25 (d, 3 H), 1 .25 (m, 1 H), 1 .19 (d, 3 H), 1.17 (d, 3 H), 0.93 (t, 3 H).

EXAMPLE 55 (11 £ 21 /?,5)-3-Decladnosil.-11.12-didosoxy-6-0-methyl- 3 -oxo-12,11-roxycarbonyl- (4- (3,4-dimethoxy-phenyl) -4-oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (3,4-dimethoxy-phenyl) -4-oxo-butyric acid (0.128 g) in D F anhydrous (9 mL) under a nitrogen atmosphere, HATU (0.205 g) and DIPEA (0.1 10 mL) were added. The reaction mixture was stirred at room temperature for 30 minutes, and then Example 6 (0.300 g) was added. The reaction mixture was stirred at room temperature for 2.5 hours, then diluted with DCM (21 mL) and washed with an aqueous solution of NaHCC > 3 to 5% (18 mL). The aqueous phase was extracted with DCM (15 mL), and the combined organic layers were dried over a2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (30 ml_) and stirred at room temperature for 24 hours. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH from 100 \ 0 \ 0 to 92 \ 8 \ 0.2), to give the title compound (0.293 g). 1 H-NMR (CDCl 3) d: 7.95 (d, NH), 7.70 (dd, 1 H), 7.55 (d, 1 H), 6.99 (d, 1 H), 5.30 (dd, 1 H), 5.30 (dd, 1 H), 4.71 (m, 1 H), 4.37 (d, 1 H), 4.08 (d, 1 H), 3.96-3.93 (m, 4 H), 3.90 (q, 1 H), 3.68 (m, 1 H), 3.39 (dd, 1 H), 3.34 (m, 2H), 3.19 (m, 1 H), 3.14 (m, 1 H), 2.75 (s, 6 H), 2.66-2.61 (m, 6 H), 2.49 (d, 1 H), 1.99-1.96 (m, 2H), 1.84-1.71 (m, 2H), 1.64 ( m, 1 H), 1.56 (s, 3 H), 1.41 (m + d, 1 H + 3 H), 1.32 (d, 3 H), 1.31 (s, 3 H), 1.26 (d, 3 H), 1.23 (d, 3 H), 1.21 (d, 3 H), 0.95 (t, 3 H). ' EXAMPLE 56 (11 ¿.21) -3-Decladinosyl-11,12-d-Deoxy-6-Q-methy1-3-oxo-12.11- [oxycarbonyl- (4- (3,4-dimethoxy-phen n-4-oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (3,4-dimethoxy-phenyl) -4-oxo-butyric acid (0.695 g) in anhydrous DMF (15 mL) under nitrogen atmosphere, HATU (1.08 g) and DIPEA (0.586 mL) were added. ). The reaction mixture was stirred at room temperature for 30 minutes, and then Example 7 (1.50 g) was added. The reaction mixture was stirred at room temperature for 18 hours, then diluted with DCM (35 mL) and washed with an aqueous solution of 5% NaHCO 3 (30 mL). The aqueous phase was extracted with DCM (25 mL), and the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (50 mL) and stirred at room temperature for 18 hours. After evaporating the solvent, the crude material was crystallized from DCM to give the title compound (1.26 g, isomer (21 S) 98% pure by NMR analysis). H-NMR (CDCl 3) dd 7.95 (d, NH), 7.70 (dd, 1 H), 7.55 (d, 1 H), 6.99 (d, 1 H), 5.30 (dd, 1 H), 5.30 (dd, 1 H), 4.71 (m, H), 4.37 (d, 1 H), 4.08 (d, 1 H), 3.96-3.93 (m, 4 H), 3.90 (q, 1 H), 3.68 (m, 1 H), 3.39 (dd, 1 H), 3.34 (m, 2H), 3.19 (m, 1 H), 3.14 (m, 1 H), 2.75 (s, 6 H), 2.66-2.61 (m, 6 H) ), 2.49 (d, 1 H), 1.99-1.96 (m, 2H), 1.84-1.71 (m, 2H), 1.64 (m, 1 H), 1.56 (s, 3 H), 1.41 (m + d, 1 H + 3 H), 1.32 (d, 3 H), 1.31 (s, 3 H), 1.26 (d, 3 H), 1.23 (d, 3 H), 1.21 (d, 3 H), 0.95 (t, 3 H).

EXAMPLE 57 i 11"£ 21 R, S) -3-Decfadinosyl-, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (4- (4-hydroxy-3-methoxy) phenyl) -4-oxo-butyramide) -methyleneol-erythromycin A To a solution of 4- (4-hydroxy-3-methoxy-phenyl) -4-oxo-butyric acid (0.922 g) in anhydrous DMF (20 mL), HOBT (0.656 g) and EDC (0.933 g) were added. Then, Example 6 (2.5 g) was added, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM (75 mL), washed with an aqueous solution of HCl at 1 N (30 mL) and then with saturated aqueous solution of NaHCO 3 (30 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 98 \ 2), and then dissolved in MeOH (10 mL) and stirred at room temperature overnight. Evaporation of the solvent gave the title compound (0.600 g). 1 H-NMR (CDC) d: 7.57 (dd, 1 H), 7.50 (d, 1 H), 6.92 (d, 1 H), 6.89 (d, 1 H), 6.05 (bs, 1 H), 5.19 (dd, 1 H), 4.80 (dd, 1 H), 4.28 (d, 1 H), 4.10 (d, 1 H), 3.93 (s, 3 H), 3.77 (q, 1 H), 3.58 (bs) , 1 H), 3.51 (m, 1 H), 3.30 (m, 2H), 3.17 (dd, 1 H), 3.06 (m, 1 H), 3.02 (m, 1 H), 2.6 (m, 3 H) ), 2.57 (s, 3 H), 2.48 (bm, 1 H), 2.41 (dd, 1 H), 2.28 (bs, 6 H), 1.95 (m, 1 H), 1.81-1.50 (m, 4 H) ), 1.47 (s, 3 H), 1.37 (d, 3 H), 1.28 (s, 3 H), 1.27 (d, 4 H), 1.22 (d, 3 H), 1.17 (d, 3 H), 1.15 (d, 3 H), 0.90 (t, 3 H).

EXAMPLE 58 (11 * 21 ^ -S-DedadinosH-H. ^ - dideoxy-eO-methyl-S-oxo- ^. H- foxycarbonyl- (4- (4-h! Droxy-3-methox! -phenyl) - 4-oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (4-hydroxy-3-methoxy-phenyl) -4-oxo-butyric acid (0.720 g) in anhydrous DMF (12 mL), HOBT (0.259 g) and EDC ( 0.368 g). Then, Example 7 (1.65 g) was added, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM (50 mL), washed with an aqueous solution of HCl at 1 N (20 mL) and then with saturated aqueous solution of NaHCO3 (20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 98 \ 2), and then dissolved in MeOH (10 mL) and stirred at room temperature overnight. The evaporation of the solvent gave e! compound of the title (0.360 g, isomer (21 or) 95% pure by NMR analysis). 1 H-NMR (CDCl 3) d: 7.57 (dd, 1 H), 7.50 (d, 1 H), 6.92 (d, 1 H), 6.89 (d, 1 H), 6.05 (bs, 1 H), 5.19 (dd, 1 H), 4.80 (dd, 1 H), 4.28 (d, 1 H), 4.10 (d, 1 H), 3.93 (s, 3 H), 3.77 (q, 1 H), 3.58 (bs) , 1 H), 3.51 (m, 1 H), 3.30 (m, 2H), 3.17 (dd, 1H), 3.06 (m, 1 H), 3.02 (m, 1 H), 2.6 (m, 3 H) , 2.57 (s, 3 H), 2.48 (bm, 1 H), 2.41 (dd, H), 2.28 (bs, 6 H), 1.95 (m, 1 H), 1.81-1.50 (m, 4 H), 1.47 (s, 3 H), 1.37 (d, 3 H), 1.28 (s, 3 H), 1.27 (d, 4 H), 1.22 (d, 3 H), 1.17 (d, 3 H), 1.15 (d, 3 H), 0.90 (t, 3 H).

EXAMPLE 59 (11 £ 21 /? 5) -3-Decladoinosyl-11, 12-d-Deoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (2- (3-methoxy-quinoxalin -2-ilsulfanyl) -acetamido) -methylene1- erythromycin A To a solution of intermediate 72 (0.032 g) in anhydrous DMF (2 mL), HATU (0.048 g) and DIPEA (0.022 mL) were added under nitrogen atmosphere. After stirring for 45 minutes, Example 7 (0.070 g) was added, and the mixture was stirred overnight. Water (5 mL) was added, and the solution was extracted with DCM (2x10 mL). The organic phase was washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (5 mL) and stirred overnight. The crude material was purified by flash chromatography (eluting with: DCM vIeOH 94 \ 6), to give the title compound (0.060 g). m \ z ([MH] +) = 859. 1 H-NMR (CDCl 3) d: 8.09 (d, 1 H), 7.78 (d, 1 H), 7.81 (d, 1 H), 7.56 (t, 1 H), 7.53 (t, 1 H), 4.65 (t, 1 H), 4.15 (s, 3 H), 4.06 (d, 1 H), 3.90 (d, 1 H), 3.03 (m, 1 H) , 2.42 (m, 1 H), 1 .10 (d, 3 H).

EXAMPLE 60 (11 *, 21?, ¾-3-Decladoinosi) -11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (quinoxalin-2-yloxy) -acetamido) -methylene-1-erythromycin A To a solution of intermediate 74 (0.038 g) in anhydrous DMF (1.5 mL), HATU (0.072 g) and DIPEA (0.033 mL) were added under nitrogen atmosphere. After stirring for 45 minutes, Example 7 (0.090 g) was added, and the mixture was stirred overnight. Water (8 mL) was added, and the solution was extracted with DCM (2x15 mL). The collected organic phases were washed with saturated aqueous solution of NaHCO 3 (10 mL) and brine (10 mL), and then dried over Na 2 SO 4 and concentrated under reduced pressure. The residue was dissolved in MeOH (5 mL) and stirred overnight. Purification of the crude material by flash chromatography (eluting with: DCM \ MeOH 95 \ 5) gave the title compound (0.047 g). m \ z ([MH] +) = 813. 1 H-NMR (CDCl 3) 5: 8.35 (s, 1 H), 7.86 (d, 1 H), 7.57 (td, H), 7.36 (m, 2H), 7.26 (d, 1 H), 5.10 (dd, 1 H), 5.02 (d, 1 H), 4.87 (d, 1 H), 3.01 (m, 1 H), 2.34 (m, 1 H), 1.1 1 (d, 3 H).

EXAMPLE 61 (11 «£ 21>« fl-3-Decladinos! [-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (4- (3-amino ^ -metox Phenyl) -4-oxo-butyramido) -methylene1- erythromycin A To a solution of Example 51 (0.070 g) in anhydrous MeOH (5 mL), palladium (10% by weight on carbon powder, 0.050 g) was added, and the mixture was stirred under a hydrogen atmosphere (1 atmosphere) for 1 hour. hour. Filtration through a pad of silica eluting with MeOH and purification by preparative TLC (eluting with: DCMVMeOH 90 \ 10), gave the title compound (0.008 g). H-NMR (CDCl 3) d: 8.47 (d, 1 H), 8.19 (d, 1 H), 7.15 (d, 1 H), 6.68 (d, 1 H), 4.82 (d, 1 H), 4.04 ( s, 3 H), 3.32 (t, 2H), 3.07 (m, 1 H), 2.70-2.60 (m, 2H), 2.39 (m, 1 H), 2.08 (s, 3 H), 1.11 (d, 3 H).

EXAMPLE 62 (11. £ 21 g) -3-Decladinosyl-11, 12-d-Deoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (4-hydroxymen-4- (4- methoxy-3-nitro-phenyl) -but! ramido) - methyleneol-erythromycin A To a solution of Example 51 (0.050 g) in anhydrous MeOH (1 mL), hydroxylamine hydrochloride (0.050 g) and ammonium acetate (0.100 g) were added. The reaction mixture was stirred at 60 ° C for 3 hours. After evaporation of the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90? 10), to give the title compound (0.015 g). 1 H-NMR (CDCl 3) d: 8.17 (d, 1 H), 7.82 (dd, 1 H), 7.13 (d, 1 H), 6.58 (bm, 1 H), 4.80 (m, 1 H), 3.00 ( m, 1 H), 3.10 (m, 2H), 2.50 (m, 2H), 2.34 (m, 1 H), 1.14 (d, 3 H).

EXAMPLE 63 (11 £ 21> 5) -3-Decidinosil-11.12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (2- (quinoxaline-2-sulfonyl) - acetamido) -met!! eno1-erythromycin A To a solution of Example 46 (0.050 g) in a 1 \ 1 mixture of water \ DCM (4 mL), magnesium monoperoxyphthalate (0.040 g) was added. After stirring for 24 hours, the aqueous phase was extracted with DCM (3x5 mL), and the organic extracts were washed with an aqueous solution of 5% Na2S205 (5 mL), dried over Na2SC > 4 and concentrated under reduced pressure. The residue was dissolved in THF (1 mL), polystyrene resin and triphenylphosphine (0.050 g) were added, and the mixture was heated at 65 ° C for 2 hours. After cooling to room temperature, the mixture was filtered and concentrated to give the title compound (0.050 g). 1 H-NMR (CDCl 3) d: 9.52 (s, 1 H), 8.24 (m, 1 H), 8.00-7.80 (m, 2 H), 7.70 (bm, 1 H), 4.83 (m, 1 H), 4.49 (d, 1 H), 4.04 (d, 1 H), 3.06 (m, 1 H), 2.50 (m, 1 H), 1.15 (d, 3 H).

EXAMPLE 64 (115: 21?,) -3-Decladoinosyl-11,12-dideoxy-6-0-metii-3-oxo-12,11-roxycarbonyl- (3-phenyl-propylamino) -methylene-erythromycin A A solution of Example 6 (0.045 g) and 3-phenyl propionaldehyde (0.010 mL) in anhydrous MeOH (1 mL) was stirred at room temperature for 1 hour under nitrogen atmosphere. Then, sodium cyanoborohydride (0.007 g) and acetic acid (0.004 mL) were added. The mixture was stirred at room temperature for 1 hour, and then the reaction was quenched with a saturated aqueous solution of NaHCO3 (2 mL). After evaporation of the solvent, the aqueous phase was extracted with DCM (3x10 mL), and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (1 mL) and stirred at room temperature overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (0.039 g). H-NMR (CDCl 3) d: 7.40-7.00 (m, 5 H), 5.74 (dd, 1 H), 4.31 (d, 1 H), 4.25 (d, 1 H), 4.13 (s, 1 H), 3.84 (q, 1 H), 3.54 (m, 1 H), 3.18 (m, 1 H), 3.11 (m, 1 H), 3.03 (m, 1 H), 2.92-2.83 (m, 2H), 2.68 (s, 3 H), 2.64 (m, 2H), 2.58 (m, 1 H), 2.46 (m, 1 H), 2.33 (m, 1 H), 2.27 (s, 6 H), 1.92 (m, 1 H), 1.76 (m, 4 H), 1.67 (m, 1 H), 1.57 (m, 1 H), 1.48 (s, 3 H), 1.38 (d, 3 H), 1 .31 (d, 3 H), 1.33 (s, 3 H), 1.25 (d, 3 H), 1.15 (d, 3 H), 1 .09 (d, 3 H), 0.87 (t, 3 H). TLC: DCM \ MeOH 10 \ 1 (Rf = 0.25).

EXAMPLE 65 (11 £ 21?, 5) -3-Decladinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (3- (4- (pyridin-3- íl) -imidazoi-1-yl) -propylamino) -methylene erythromycin A A solution of Example 6 (0.100 g) and intermediate 52 (0.040 g) in anhydrous DCM (4 mL) was stirred at room temperature for 6 hours under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.150 mL) and acetic acid (0.009 mL) were added, and the mixture was stirred for 48 hours. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL) and extracted with DCM (3x15 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (5 mL) and heated at reflux temperature for 48 hours. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 90 \ 10), to give the title compound (0.008 g). 1 H-NMR (CDCl 3) d: 9.00 (d, 1 H), 8.45 (d, 1 H), 8.1 1 (d, 1 H), 7.59 (d, 1 H), 7.39 (d, 1 H), 7.29 (m, 1 H), 5.55 (dd, 1 H), 4.29 (d, 1 H), 4.24 (d, 1 H), 4.13 (s, 1 H), 4.20-4.0 (m, 2H), 3.86 ( q, 1 H), 3.55 (m, 1 H), 3.19 (m, 1 H), 3.09 (m, 1 H), 3.05 (m, 1 H), 2.93 (m, 2H), 2.67 (s, 3 H), 2.52 (m, 1 H), 2.49 (m, 1 H), 2.32 (d, 1 H), 2.27 (s, 6 H), 2.02 (m, 1 H), 1.94 (m, 2H), 1.80 (m, 2H), 1.65 (m, 1 H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.33 (s, 3 H), 1 .31 (d, 3 H), 1.25 (m, 1 H), 1.24 (d, 3 H), 1 .16 (d, 3 H), 1 .09 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 66 (11, 2) -3-Decladinosyl-11, 12-d-Deoxy-6-O-methyl-3-oxo-12,11-roxycarbonyl- (3- (4- (pyridin-3-yl) - imidazol-1-yl) -propylamino) -rnetylene -T- erythromycin A A solution of Example 7 (0.500 g) and intermediate 52 (0.180 g) in anhydrous acetonitrile (7 mL) was stirred at room temperature for 2 hours under nitrogen atmosphere. The solvent was evaporated, and the residue was dissolved in anhydrous MeOH (5 mL). Then, sodium cyanoborohydride (1 M in THF, 0.375 mL) and acetic acid (0.045 mL) were added under nitrogen atmosphere, and the mixture was stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL) and extracted with DCM (3x15 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound (0.170 g, 95% pure (21 S) isomer by NMR analysis). 1 H-NMR (CDCl 3) d: 9.00 (d, 1 H), 8.45 (d, 1 H), 8.1 1 (d, 1 H), 7.59 (d, 1 H), 7.39 (d, 1 H), 7.29 (d. m, 1 H), 5.55 (dd, 1 H), 4.29 (d, 1 H), 4.24 (d, 1 H), 4.13 (s, 1 H), 4.20-4.0 (m, 2H), 3.86 (q , 1 H), 3.55 (m, 1 H), 3.19 (m, 1 H), 3.09 (m, 1 H), 3.05 (m, 1 H), 2.93 (m, 2H), 2.67 (s, 3 H) ), 2.52 (m, 1 H), 2.49 (m, 1 H), 2.32 (d, 1 H), 2.27 (s, 6 H), 2.02 (m, 1 H), 1.94 (m, 2H), 1.80 (m, 2H), 1.65 (m, H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.33 (s, 3 H), 1.31 (d, 3 H), 1.25 (m, 1 H), 1.24 (d, 3 H), 1.16 (d, 3 H), 1.09 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 67 (11. £ 21 / P ^ -S-Decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-phoxycarboryl- (4- (4- (pyridin-3-in- imidazol-1-yl) -butylamino) -methylene] - erythromycin A A solution of Example 6 (0.100 g) and intermediate 54 (0.050 g) in anhydrous DCM (3 mL) was stirred at room temperature for 24 hours under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.120 mL) and acetic acid (0.008 mL) were added under a nitrogen atmosphere, and the mixture was stirred for 1 hour. The reaction was quenched with saturated aqueous NaHCO3 solution (5 mL) and extracted with DCM (3x10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM leOH from 95 \ 5 to 90 \ 10), to give a compound which was dissolved in MeOH (2 mL) and stirred at room temperature overnight. The evaporation of the solvent under reduced pressure, gave the title compound (0.015 g). 1 H-NMR (CDCl 3) d: 8.98 (d, 1 H), 8.46 (d, 1 H), 8.09 (d, 1 H), 7.56 (d, 1 H), 7.36 (d, 1 H), 7.30 (m, 1 H), 5.67 (dd, 1 H), 4.30 (d, 1 H), 4.24 (d, 1 H), 4.13 (s, 1 H), 4.00 (m, 2H), 3.85 (q, 1 H), 3.56 (m, 1 H), 3.19 (m, 1 H), 3.09 (m, 1 H), 3.03 (m, 1 H), 2.91 (m, 2 H), 2.64 (s, 3 H) , 2.58 (m, 1 H), 2.47 (m, 1H), 2.28 (m + s, 6 H +1 H), 2.00 (m, 1 H), 1.89 (m, 2H), 1.79 (m, 1 H ), 1.70 (m, 2H), 1.60-1.50 (m, 2H), 1.48 (s, 3 H), 1.39 (d, 3 H), 1.31 (s, 3 H), 1.31 (d, 3 H) ), 1.25 (d, 3 H), 1.25 (m, 1 H), 1.15 (d, 3 H), 1.09 (d, 3 H), 0.83 (t, 3 H).

EXAMPLE 68 (11 «9.21 P, 5) -3-Decladinosl-11,12-dideoxy-6-Q-methyl-3-oxo-12.11-roxycarbonyl-f5- (4- (pyridine- 3-yl) -imidazoM -H) -pentylamino) -methylene-erythromycin A A solution of Example 6 (0.080 g) and intermediate 56 (0.042 g) in anhydrous DCM (5 mL) was stirred at room temperature for 1 hour under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.120 mL) and HCl (2N in Et20, 0.010 mL) were added under a nitrogen atmosphere, and the mixture was stirred for 1 hour. The reaction was quenched with saturated aqueous NaHCC solution (10 mL) and extracted with DCM (3x15 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with DCM IeOH from 96V4 to 90 \ 10), to give a compound which was dissolved in MeOH (3 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.013 g). 1 H-NMR (CDCl 3) d: 8.99 (d, 1 H), 8.47 (d, 1 H), 8.10 (d, 1 H), 7.55 (s, 1 H), 7.31 (s, 1 H), 7.29 (m, 1 H), 5.67 (d, 1 H), 4.30 (d, 1 H), 4.25 (d, 1 H), 4.1 1 ( s, 1 H), 3.96 (m, 2H), 3.85 (q, 1 H), 3.58 (m, 1 H), 3.18 (dd, 1 H), 3.09 (m, 1 H), 3.02 (m, 1 H), 2.90-2.75 (m, 2H), 2.67 (s, 3 H), 2.58 (m, 1 H), 2.46 (s, 1 H), 2.29 (d, 1 H), 2.27 (s, 6 H) ), 1.90-1.86 (m, 3 H), 1.78 (m, 1 H), 1.70 (m, 2H), 1.60-1.50 (m, 3 H), 1.47 (s, 3 H), 1.5-1.4 (m , 4 H), 1.38 (d, 3 H), 1.33 (s, 3 H), 1.32 (d, 3 H), 1.28 (d, 3 H), 1 .25 (m, 1 H), 1 .15 (d, 3 H), 1.09 (d, 3 H), 0.85 (t, 3 H).

EXAMPLE 69 (11. £ 21 £ «S) -3-Decladinosl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (2- (4- (pyridin-3 -yl) -imidazol-1-yl) -tylamino) -methylene] - erythromycin A A solution of intermediate 51 (0.040 g) in acetonitrile (1 mL) and an aqueous solution of HCI at 2M (3 mL) was heated at 80 ° C for 3 hours. The reaction mixture was allowed to reach room temperature, and then it was added dropwise to a solution of Example 6 (0.100 g) dissolved in anhydrous acetonitrile (4 mL), maintaining the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCOs. The solution was stirred at room temperature for 2 hours. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.150 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCC > 3 (5 mL), and the product was extracted with DCM (3x10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material purified by flash chromatography (eluting with DCM \ MeOH 94 \ 6), gave the title compound (0.027 g). 1 H-NMR (CDCl 3) d: 9.04 (d, 1 H), 8.46 (dd, 1 H), 8.12 (d, 1 H), 7.61 (d, 1 H), 7.56 (m, 1 H), 7.30 (m , 1 H), 5.63 (dd, 1 H), 4.27 (d, 1 H), 4.22 (d, 1 H), 4.19 (d, 1 H), 4.20-4.08 (m, 2H), 3.84 (q, 1 H), 3.54 (m, 1 H), 3.36-3.19 (m, 2H), 3.16 (dd, 1 H), 3.05 (m, 2H), 2.55 (m, 1 H), 2.44 (m, 1 H) ), 2.43 (s, 3 H), 2.28 (s, 1 H), 2.27 (s, 6 H), 1.85 (m, 1 H), 1.75 (m, 1 H), 1 .70-1.65 (m, 2H), 1.55 (m, 1 H), 1.48 (s, 3 H), 1.40 (d, 3 H), 1.30 (d, 3 H), 1.24-1.20 (m, 4 H), 1.23 (s, 3 H), 1.14 (d, 3 H), 1.09 (d, 3 H), 0.82 (t, 3 H).

EXAMPLE 70 foxicarbonyl- (2- (4- (pyridin-3 l) -imidazole erythromlcin A A solution of intermediate 51 (0.530 g) in acetonitrile (30 mL) and an aqueous solution of 3M HCl (20 mL) was heated at 80 ° C for 3 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 7 (0.500 g) dissolved in anhydrous acetonitrile (2 mL), maintaining the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCO 3. The solution was stirred at room temperature for 1 hour. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.75 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous NaHCC solution was added >; 3 (15 mL), and the mixture was extracted with DCM (3x20 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (10 mL) and stirred overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with DCM \ MeOH from 98 \ 2 to 90 \ 10), to give the title compound (0.350 g, 95% pure (2 S) isomer). by NMR analysis). 1 H-NMR (CDCl 3) d: 9.04 (d, 1 H), 8.46 (dd, 1 H), 8.12 (d, 1 H), 7.61 (d, 1 H), 7.56 (m, 1 H), 7.30 (m , 1 H), 5.63 (dd, 1 H), 4.27 (d, 1 H), 4.22 (d, 1 H), 4.19 (d, 1 H), 4.20-4.08 (m, 2H), 3.84 (q, 1 H), 3.54 (m, 1 H), 3.36-3.19 (m, 2H), 3.16 (dd, 1 H), 3.05 (m, 2H), 2.55 (m, 1 H), 2.44 (m, 1 H) ), 2.43 (s, 3 H), 2.28 (s, 1 H), 2.27 (s, 6 H), 1.85 (m, 1 H), 1.75 (m, 1 H), 1.70-1.65 (m, 2H), 1 .55 (m, 1 H), 1.48 (s, 3 H), 1.40 (d, 3 H), 1.30 (d, 3 H), 1.24-1.20 (m, 4 H), 1.23 (s) , 3 H), 1.14 (d, 3 H), 1.09 (d, 3 H), 0.82 (t, 3 H).

EXAMPLE 71 (11 21 /), S-3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-oxocarbonyl- (5- (quino [in ^ H]) - pentnamino) -methyleneI ^ ritromycin A A solution of Example 6 (0.084 g) and intermediate 63 (0.040 g) in anhydrous DCM (4 mL) was stirred at room temperature for 1 hour under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.125 mL) and acetic acid (0.007 mL) were added, and the mixture was stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL) and extracted with DCM (3x10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with DCMWleOH 90 \ 10), to give a compound which was dissolved in MeOH (3 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.006 g). 1 H-NMR (CDCIS) d: 8.81 (d, 1 H), 8.1 1 (d, 1 H), 8.06 (d, 1 H), 7.70 (t, 1 H), 7.57 (t, 1 H), 7.26 (d, 1 H), 5.71 (dd, 1 H), 4.31 (d, 1 H), 4.26 (d, 1 H), 4.12 (d, 1 H), 3.85 (q, 1 H), 3.55 ( m, 1 H), 3.19 (m, 1 H), 3.10 (m, 1 H), 3.07 (m, 2H), 3.03 (m, 1 H), 2.90 (m, 1 H), 2.80 (m, 1 H), 2.68 (s, 3 H), 2.58 (m, 1 H), 2.45 (m, 1 H), 2.30 (d, 1 H), 2.27 (s, 6 H), 1.90 (m, 1 H), 1.75 (m, 2H), 1.70 (m, 3 H), 1.52 (m, 2H), 1.48 (s, 3 H), 1.37 (d, 3 H), 1.33 (s, 3 H), 1.32 (d, 3 H), 1.24 (m, 1 H), 1 .25 (d, 3 H), 1.15 (d, 3 H), 1.09 (d, 3 H), 0.85 (t, 3 H).

EXAMPLE 72 (11.9.2 7?) -3-Decladoinosyl-1, 12-dideoxy-6-Q-metM-3-oxo-12,11-foxycarbonyl-f3- (qu! NoHn ^ -H) -prophamyl) -methylenol-er? thromycin A A solution of Example 6 (0.100 g) and 3-quinolin-4-yl-propionaldehyde (0.031 g) in anhydrous DCM (4 mL) was stirred at room temperature for 2 hours under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.150 mL) and acetic acid (0.009 mL) were added, and the mixture was stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL) and extracted with DCM (3x10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with DCM \ MeOH 95 \ 5), to give a compound which was dissolved in MeOH (3 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.011 g). 1 H-NMR (CDCl 3) d: 8.80 (d, 1 H), 8.13-8.09 (d, 2 H), 7.70 (t, 1 H), 7.58 (t, 1 H), 7.30 (m, 1 H), 5.80 (dd, 1 H), 4.31 (d, 1 H), 4.26 (d, 1 H), 4.19 (s, 1 H), 3.86 (q, 1 H), 3.56 (m, 1 H), 3.50 ( bm, 1 H), 3.26 (m, 1 H), 3.19 (m, 1 H), 3.12 (m, 1 H), 3.06 (m, 3 H), 2.90 (m, 1 H), 2.69 (s, 3 H), 2.58 (m, 1 H), 2.46 (m, 1 H), 2.36 (d, 1 H), 2.27 (s, 6 H), 1.92 (m, 3 H), 1.80-1.70 (m, 2H), 1.65 (m, 1 H), 1.60 (m, 1 H), 1.50 (s, 3 H), 1.40 (d, 3 H), 1.33 (s + d, 3H + 3 H), 1 .24 (m, 4 H), 1.16 (d, 3 H), 1.1 1 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 73 (11 £ 21?,?) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11-roxycarbonH- (4-fquinol-yrt-4-yl) -butiiammo) - Fnetylene? -erythromycin A A solution of Example 6 (0.130 g) and intermediate 59 (0.047 g) in anhydrous THF (5 mL) was stirred at room temperature for 1 hour under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.195 mL) and acetic acid were added until pH = 5, and the mixture was stirred for 3 hours. The reaction was quenched with saturated aqueous NaHCO3 solution (10 mL) and extracted with DCM (3x10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with DCM \ MeOH from 98 \ 2 to 96 \ 4), to give a compound that was dissolved in MeOH (5 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.015 g). m \ z ([MH] +) = 810.

EXAMPLE 74 (11 £ 21 /?) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (quinolin '-yl) -ethylamino) - methylene1-eritrornicin A A solution of intermediate 57 (0.270 g) in acetonitrile (4 mL) and an aqueous solution of 3M HCl (4 mL) was heated at 50 ° C for 24 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 6 (0.500 g) in anhydrous acetonitrile (4 mL), maintaining the pH of the solution on the scale of 6-7. by the addition of saturated aqueous solution of NaHCO3. The solution was stirred at room temperature for 3 hours. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.75 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCO3 (15 mL) was added, and the mixture was extracted with DCM (3x20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in MeOH (10 mL) and stirred overnight. After evaporation of the solvent, the crude material was purified by flash chromatography (eluting with DCMWleOH from 98 \ 2 to 90 \ 10), to give the title compound (0.190 g). 1 H-NMR (CDCl 3) d: 8.79 (d, 1 H), 8.09 (m, 1 H), 7.69 (t, 1 H), 7.56 (t, 1 H), 7.38 (d, 1 H), 5.68 (dd, 1 H), 4.29 (d, 1 H), 4.22 (d, 1 H), 4.21 (s, 1 H), 3.83 (q, 1 H), 3.54 (m, 1 H), 3.41-3.1 (m, 4 H), 3.17 (dd, 1 H), 3.07 (m, 1 H), 3.02 (m, 1 H), 2.45 (m, 2H + -OCH3), 2.30 (m, 1 H), 2.27 (s, N (CH3) 2), 1.88 (m, 1 H), 1.75 (m, 2H), 1.66 (m, 1 H), 1.55 (m, 1 H), 1.47 (s, 3 H), 1 .37 (d, 3 H), 1.30 (d, 3 H), 1.25 (d, 3 H), 1.25 (m, 4 H), 1.12 (d, 3 H), 1.08 (d, 3 H), 0.85 (t, 3 H).

EXAMPLE 75 (11 £ 21) -3-Declado-nosii-l 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (2- (quinolin-H) ^ t -lamino) - methylen] -ertromine A A solution of intermediate 57 (0.832 g) in acetonitrile (16 ml_), and an aqueous solution of 3M HCl (16 ml_), were heated at 50 ° C for 16 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 7 (1500 g) in anhydrous acetonitrile (12 mL), maintaining the pH of the solution on the scale of 6-7. by the addition of saturated aqueous solution of NaHCO3. The solution was stirred at room temperature for 1 hour. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (M in THF, 3.3 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, water (100 mL) was added, and the mixture was extracted with EtOAc (2x100 mL). The organic layer was dried over a2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (DCM \ MeOH 95 \ 5). The obtained compound was dissolved in MeOH (20 mL) and stirred overnight. After evaporation of the solvent, the compound was purified by flash chromatography (eluting with DCM \ MeOH 95 \ 5), to give the title compound (0.365 g, 95% pure isomer (215) by NMR analysis). 1 H-NMR (CDCl 3) 5: 8.79 (d, 1 H), 8.09 (m, 1 H), 7.69 (t, 1 H), 7.56 (t, 1 H), 7.38 (d, 1 H), 5.68 (d. dd, 1 H), 4.29 (d, 1 H), 4.22 (d, 1 H), 4.21 (s, 1 H), 3.83 (q, 1 H), 3.54 (m, 1 H), 3.41-3.1 ( m, 4 H), 3.17 (dd, 1 H), 3.07 (m, 1 H), 3.02 (m, 1 H), 2.45 (m, 2H + 3 H), 2.30 (m, 1 H), 2.27 ( s, 6 H), 1.88 (m, 1 H), 1.75 (m, 2H), 1.66 (m, 1 H), 1.55 (m, 1 H), 1.47 (s, 3 H), 1.37 (d , 3 H), 1.30 (d, 3 H), 1.25 (d, 3 H), 1.25 (m, 4 H), 1.12 (d, 3 H), 1.08 (d, 3 H), 0.85 (t, 3 H).

EXAMPLE 76 (11 £ 21) -3-Decladinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbon) l- (fquinolin ^ -yl) -methylamino) -methylene1- erythromycin A A solution of example 7 (0.050 g) and quinoline-4-carbaldehyde (0.020 g) in anhydrous toluene (3 mL), was stirred at 100 ° C for 16 hours under nitrogen atmosphere. After evaporation of the solvent, the crude material was dissolved in anhydrous MeOH (5 mL), palladium (10% by weight on carbon powder, 0.006 g) was added, and the mixture was stirred under a hydrogen atmosphere (1 atmosphere) for 5 hours. Filtration through a pad of celite eluting with MeOH, and purification by flash chromatography (eluting with: DCMWIeOH 93 \ 7), gave the title compound (0.007 g). m \ z ([MH] +) = 768. 1 H-NMR (CDCl 3) d: 8.89 (d, 1 H), 8.1 1 (d, 1 H), 8.09 (d, 1 H), 7.69 (t, 1 H), 7.60 (t, 1 H), 7.56 (t, 1 H), 4.65 (m, 1 H), 4.48 (m, H), 4.38 (m, 1 H), 3.09 (m, 1 H) , 2.43 (m, 1 H), 1.14 (d, 3 H).

EXAMPLE 77 (11 £ 21 / ?,.S) 3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11-foxycarbonyl- (3- (5-methyl-furan-2-M) ) -butylamino) -methylene-1-erythromycin A A solution of 3- (5-methyl-2-furyl) butanal (0.030 g) and example 6 (0.067 g) in anhydrous acetonitrile (1 mL), was stirred at room temperature for 5 hours under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.250 mL) and acetic acid (0.025 mL) were added, and the mixture was stirred at room temperature for 24 hours. MeOH (1 mL) was added, and the reaction mixture was heated at 60 ° C for 24 hours. After evaporation under reduced pressure, the residue was dissolved in DCM (10 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with: DC \ eOH \ NH4OH 95 \ 5 \ 0.5), to give the title compound (0.029 g). 1 H-NMR (CDCl 3) d: 5.82 (m, 2 H), 4.10 (m, 1 H), 3.02 (m, 1 H), 2.86 (s, 2 H), 2.77 (m, 1 H), 2.40-2.20 (m, 3H + 1 H), 1.80-1.60 (m, 2H), 1.08 (d, 3 H).

EXAMPLE 78 f 1 «- > , 21 P, "S) -3-Decladoinosyl-11, 12-cydesoxy-6-0-methyl-3-oxo-12,11-roxycarboni [- (3-pyridin-2-prop-2-n-amino) - methyleneol-erythromlcin A A solution of 3- (5-rnethyl-2-furyl) butanal oxalate (0.045 g), Example 6 (0.067 g) and DIPEA (0.051 mL) in anhydrous acetonitrile (1 mL), was stirred at room temperature for 1.5 hours under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.250 mL) and acetic acid (0.025 mL) were added, and the mixture was stirred at room temperature for 15 hours. MeOH (1 mL) was added, and the reaction mixture was heated at 60 ° C for 48 hours. After evaporation under reduced pressure, the residue was dissolved in DCM (10 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over NaSO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DC, DC \ MeOH \ NH4OH from 96 \ 4 \ 0.1 to 92 \ 8 \ 0.2), to give the title compound (0.016 g). m \ z ([MHf) = 744. 1 H-NMR (CDCIs) d: 8.52 (d, 2H), 7.28 (d, 2H), 6.59 (dd, 2H), 4.24 (m, 11-1), 3.65 (m, 2H), 3.05 (m, 1 H), 2.38 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 79 (11 «¾21 g> -3-Decafadinosyl-11, 2-dideoxy-6-Q-metii-3-oxo-12,11-roxycarbonyl- (3- (4- (3,5-difluoro-phenyl) ) -pyrazol-1 -ii) -propylamino) -methylene '| - erythromycin A To a solution of Example 7 (0.030 g) in anhydrous THF (1 mL), intermediate 75 (0.050 g) was added, and the mixture was stirred at room temperature for 3 hours under nitrogen atmosphere. Then, sodium cyanoborohydride (1 M in THF, 0.150 mL) and acetic acid (0.010 mL) were added, and the mixture was allowed to react for 4 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in MeOH (1 mL), and the mixture was stirred overnight. After evaporation of the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound ((0.014 g) .1 H-NMR (CDCl3) d: 7.83 (s, 1 H), 7.73 (s, 1H), 7.03 (dd, 1 H), 6.62 (tt, 1H), 4.28 (m, 2H), 4.12 (s, 1 H), 3.04 (m, 1 H) ), 2.91 (m, 1 H), 2.82 (m, 1 H), 2.32 (bs, 2H), 2.07 (m, 1 H), 2.00 (m, 1 H), 1.09 (d, 3 H).

EXAMPLE 80 (11 £ 21 ?,) -3-Decladinosil-11, 12-d! Deoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (3-f4- (4-chloro-phen L) -2,5-dimethyl-imidazol-1-yl) -propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 76 (0.025 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 5 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the residue was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1 M in THF) was added., 0.037 mL) and acetic acid (0.005 mL). After 18 hours, the solvent was evaporated under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (0.028 g). 1 H-NMR (CDCl 3) d: 7.55 (d, 2 H), 7.33 (d, 2 H), 4.15 (m, 1 H), 4.00 (m, 1 H), 3.85 (m, 1 H), 3.05 (m , H), 3.02-2.90 (m, 2H), 2.42 (s, 3 H), 2.35 (s, 3 H), 2.33 (m, 1 H), 1.90 (m, 1 H), 1.72 (m, 1 H), 1.09 (d, 3 H).

EXAMPLE 81 (11, 21 /?) -3-DecladinosM 1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl-f3- (4- (4-nitro-phenyl) -imidazoM -yl) -propylamino) -methylene-1-erythromycin A A solution of Example 7 (0.050 g) and intermediate 77 (0.023 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.005 mL) were added. After 24 hours, the solvent was evaporated under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of aHC03 (2x3 mL). The organic phase was dried over a2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (0.007 g). 1 H-NMR (CDC) 5: 8.24 (d, 2H), 7.96 (d, 2H), 7.61 (d, 1 H), 7.54 (d, 1 H), 4.14 (m, 1 H), 4.20 ÷ 4.06 (m, 2H), 3.00 ÷ 2.88 (m, 2H), 2.32 (m, 1 H), 2.03 (m, 1 H), 1.92 (m, 1 H).

EXAMPLE 82 (11 *, 21.7.5) -3-Declac »nosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12.11 - [oxycarbonyl-f3- (4 ^ iridin ^ -yl-imidazole- 1-H) -propylamine) -methylene-1-erythromycin A A solution of Example 7 (0.050 g) and intermediate 78 (0.025 g) in anhydrous acetonitrile (2 mL) was stirred at room temperature for 16 hours under nitrogen atmosphere, and then heated at 50 ° C for 4 hours. After evaporating the solvent under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.100 mL) and acetic acid (0.006 mL) were added. After 24 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 90M0), to give the title compound (0.014 g). 1 H-NMR (CDCl 3) d: 8.57 (d, 1 H), 7.70 (d, 1 H), 7.62 (s, 1 H), 7.52 (s, 1 H), 4.20-4.16 (m, 2H), 3.05 (m, 1 H), 2.96-2.88 (m, 2H), 2.32 (m, 1 H), 2.02-1.92 (m + m, 2H), 1.10 (d, 3 H).

EXAMPLE 83 (11 £ 21R,) -3-Decladoinosyl-11, 12-d-Desoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (3- (3-trifluoromethyl-1 yypyrazole) 4-yl) -propylamino) -metholene V erythromycin A A solution of Example 7 (0.020 g) and intermediate 79 (0.015 g) in anhydrous acetonitrile (2 mL) was stirred at room temperature for 3 hours under nitrogen atmosphere, and then heated at 40 ° C for 4 hours. After evaporating the solvent under reduced pressure, the crude material was dissolved in anhydrous eOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.015 mL) and acetic acid (0.003 mL) were added. After 24 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DC VIeOH from 100 \ 0 to 98 \ 2), to give the title compound (0.004 g). 1 H-NMR (CDCl 3) d: 7.53 (s, 1 H), 4.12 (d, 1 H), 3.03 (m, 1 H), 2.92 (m, 1 H), 2.84 (m, 1 H), 2.70 -2.60 (m, 2H), 2.11 (m, 1 H), 1.70 (m, 2H), 1.09 (d, 3 H).

EXAMPLE 84 (11 S, 2?,. Fl-3-Decladoinosyl-11, 12-diodeoxy-6-0-methy1-3-oxo-12,11-roxycarbonyl- (3-f5-methyl-4- (4 -trifluoroethyl-phenyl) -mydazol-1-SI) -propylamino) -methylene T-erythromycin A A solution of Example 7 (0.050 g) and intermediate 80 (0.038 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature overnight under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1 mL), and then sodium cyanoborohydride (1 M in THF) was added., 0.037 mL) and acetic acid (0.004 mL). After 24 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH from 98 \ 2 \ 0 to 95 \ 5 \ 0.5) and by preparative TLC (DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the title compound (0.017 g). 1 H-NMR (CDCl 3) d: 7.78 (d, 2H), 7.64 (d, 2H), 7.59 (s, 1 H), 5.60 (dd, 1H), 4.30 (d, 1 H), 4.25 (d. d, 1 H), 4.15 (s, 1 H), 4.10 (m, 1 H), 3.96 (m, 1 H), 3.86 (q, 1 H), 3.56 (m, 1 H), 3.19 (dd, 1 H), 3.09 (m, 1 H), 3.04 (m, 1 H), 2.96 (m, 2 H), 2.68 (s, 3 H), 2.58 (m, 1 H), 2.45 (m, 1 H) , 2.42 (s, 3 H), 2.33 (s, 1 H), 2.27 (s, 6 H), 2.00 ÷ 1.88 (2 H), 1.90 (m, 1 H), 1.81 (dd, 1 H), 1.73 ( bd, 1 H), 1.67 (m, 1 H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1.38 (d, 3 H), 1.34 (s, 3 H), 1.32 (d, 3 H), 1.25 (m, 1 H), 1.25 (d, 3 H), 1.16 (d, 3 H), 1.10 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 85 (11.?, 21 /?,. S) -3-Decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12.11-foxycarbonyl- (3- (p! Ridin-3-yl) ) -propylamino) -methylene-1-erythromycin A A solution of Example 7 (0.050 g) and intermediate 81 (0.020 g) in anhydrous acetonitrile (0.7 mL) was stirred at room temperature for 3 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1 mL), and then sodium cyanoborohydride (1 M in THF, 0.035 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (0.009 g). m \ z ([MH] +) = 746. 1 H-NMR (CDCl 3) d: 8.47-8.40 (m, 2H), 7.51 (m, 1 H), 7.19 (m, 1 H), 4.14 (m, 1 H), 3.03 (m, 1 H), 2.98-2.85 (m, 2H), 2.75-2.60 (m, 2H), 2.31 (bm, 1 H), 1.82-1.76 (m, 2H), 1 .09 (d, 3 H).

EXAMPLE 86 (11, 21 >?, 5) -3-Decladoinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (4-pyridin-2-yl) -pyrazol-1-yl) -propylamino) -rnetylene1-erythromycin A A solution of Example 7 (0.050 g) and intermediate 82 (0.025 g) in anhydrous acetonitrile (3 mL) was stirred at 50 ° C for 3 hours and at room temperature overnight under a nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2.2 mL), and then sodium cyanoborohydride (1 M in THF, 0.040 mL) and acetic acid (0.020 mL) were added. After 10 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH 95 \ 5), to give the title compound (0.026 g). 1 H-NMR (CDCl 3) d: 8.54 (d, 1 H), 8.01 (s, 1 H), 7.98 (s, 1 H), 7.65 (t, 1 H), 7.50 (t, 1 H), 7.07 (m, 1 H), 4.27 (d, 1 H), 4.14 (m, 2 H), 3.04 (m, 1 H), 2.89 (m, 2 H), 2.34 (m, 1 H), 2.12 (m, 1 H), 2.03 (m, 1 H), 1.09 (d, 3 H).

EXAMPLE 87 f 11 £ 21R, 5) -3-Decladoinosyl-11, 12-d-Deoxy-6-Q-methyl-3-oxo-12,11 - [oxycarbonyl- (3- (pyridin-4-yl) -propylamine) -methylene-1-erithromic A A solution of Example 7 (0.050 g) and intermediate 83 (0.050 g) in anhydrous acetoniton (1 mL) was stirred at room temperature overnight under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 24 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 90 \ 10) and by preparative TLC (eluting with: DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the compound of the title (0.014 g). H-NMR (CDCl 3) d: 8.47 (d, 2H), 7.13 (d, 2H), 5.70 (dd, 1 H), 4.31 (d, 1 H), 4.25 (d, 1 H), 4.14 (s, 1 H), 3.85 (q, 1 H), 3.56 (m, 1 H), 3.18 (dd, 1 H), 3.10 (m, 1 H), 3.03 (q, 1 H), 2.95 ÷ 2.83 (m, 2H), 2.65 ÷ 2.55 (m, 2H), 2.67 (s, 3 H), 2.59 (m, H), 2.46 (s, 1 H), 2.31 (s, 1 H), 2.27 (s, 6 H) , 1.91 (m, 1 H), 1.82 ÷ 1.76 (m, 3 H), 1.73 (m, 1 H), 1.68 (m, 1 H), 1.58 (m, 1 H), 1.48 (s, 3 H) , 1.39 (d, 3 H), 1 .34 (s, 3 H), 1.32 (d, 3 H), 1 .25 (m, 1 H), 1.25 (d, 3 H), 1.15 (d, 3 H), 1 .09 (d, 3 H), 0.87 (t, 3 H).

EXAMPLE 88 (11 £ 21> 5) -3-Decladinosyl-11, 12-d-deoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl-f3-f4-pyrim D < -yl-pyrazole-1-8l) -propylamine) -methyllenol-erythromycin A A solution of Example 7 (0.028 g) and intermediate 84 (0.018 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 30 minutes, and then heated at 50 ° C for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.025 mL) and acetic acid (0.004 mL) were added. After 24 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 97 \ 3), to give the title compound (0.005 g). 1 H-NMR (CDCl 3) d: 9.09 (d, 1 H), 8.63 (d, 1 H), 8.18 (s, 1 H), 8.07 (s, 1 H), 7.47 (d, 1 H), 4.30 (m, 2H), 4.13 (s, 1 H), 3.04 (m, 1 H), 2.92-2.80 (m, 2H), 2.33 (m, 1 H), 2.11 (m, 1 H), 2.00 (m , 1 H), 1.09 (d, 3 H).

EXAMPLE 89 (11, 21?,. Fl-3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (3- (4-pyridin-4-y! l-pyrazol-1-yl) -propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 85 (0.018 g) in anhydrous acetonitrile (2.2 mL) was stirred at 50 ° C for 16 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous eOH (3 mL), and then sodium cyanoborohydride (1 M in THF, 0.040 mL) and acetic acid (0.020 mL) were added. After 18 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with a saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 95 \ 5), to give the title compound (0.014 g). 1 H-NMR (CDCIS) d: 8.55 (d, 1 H), 7.96 (s, 1 H), 7.85 (s, 1 H), 7.42 (d, 1 H), 4.13 (d, 1 H), 3.04 (m, 1 H), 2.89 (m, 1 H), 2.84 (m, 1 H), 2.33 (m, 1 H), 2.10 (m, 1 H), 1.95 (m, 1 H), 1.10 (d) , 3 H).

EXAMPLE 90 (11 £ 21 «S) -3-Decladinosyl-11,12-dideoxy-6-Q-metH-3-oxo-12,11-hydroxycarbonyl- (3- (4- (3,5 -dichloro-phenH) -2,5-dimethyl-imidazol-1-yl) -propylamino) -methylene-1-erythromycin A A solution of Example 7 (0.030 g) and intermediate 86 (0.029 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 5 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1M in THF, 0.022 mL) and acetic acid (0.003 mL) were added. After 12 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and. it was washed with saturated aqueous solution of NaHCO3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100? 0 to 97 \ 3), to give the title compound (0.022 g). 1 H-NMR (CDCl 3) d: 7.47 (d, 2H), 7.15 (t, 1 H), 4.11 (m, 1 H), 3.98 (m, 1 H), 3.82 (m, 1H), 2.93 (m , 2H), 2.38 (s, 3 H), 2.33 (s, 3 H), 2.29 (m, 1H), 1.6-5-1.8 (m, 2H).

EXAMPLE 91 (11:.??,) -3-Decladinosyl-11, 12-dideoxy-6-Q-methy [-3-oxo-12,11-roxycarbonyl-f3- (2,5-dimetiM- (3- trifluoromethyl-phenyl) -imidazol-1-in-propylamino) -methylene-1-erythromycin A A solution of Example 7 (0.040 g) and intermediate 87 (0.042 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 4 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1 M in THF, 0.030 mL) and acetic acid (0.004 mL) were added. After 12 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DC \ MeOH from 100 \ 0 to 97 \ 3), to give the title compound (0.026 g). 1 H-NMR (CDC! 3) d: 7.84 (bs, 1 H), 7.74 (m, 1 H), 7.43 (m, 2 H), 4.12 (s, 1 H), 3.99 (m, 1 H), 3.82 (m, 1 H), 2.9 ÷ 2.88 (m, 2H), 2.40 (s, 3 H), 2.33 (s, 3 H), 2.30 (s, 1 H), 1.85 ÷ 1.75 (m, 2H).

EXAMPLE 92 (11, 21?, 5) -3-DecladoinsH-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11-roxycarbonyl- (3-r4- (1,3-benzoxazole-2-H ) -1 pyrazoi-1-α-propylamino) - methyleneol-erythromycin A A solution of Example 7 (0.037 g) and intermediate 88 (0.022 g) in anhydrous acetonitrile (1.5 mL) was stirred at 50 ° C for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.030 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 97 \ 3), to give the title compound (0.007 g). 1 H-NMR (CDCl 3) d: 8.17 (s, 1 H), 8.14 (s, 1 H), 7.68 (d, 1 H), 7.51 (dd, 1 H), 7.29 (m, 2 H), 4.34- 4.29 (m, 2H), 4.14 (s, 1 H), 3.03 (m, 1 H), 2.90 (m, 2H), 2.33 (bm, 1 H), 2.15 (m, 1 H), 2.00 (m, 1 H), 1.09 (d, 3 H) EXAMPLE 93 f11, 21 > ?,) -3-Decladoinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (5-pyridin-1-yl-pyrazoyl-1-yl) ^ ropylamino) -methylene1- erythromycin A A solution of Example 7 (0.050 g) and intermediate 89 (0.036 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 20 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 in THF, 0.075 mL) and acetic acid (0.010 mL) were added. After 20 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWIeOH from 100 a to 97 3), to give the title compound (0.011 g). i H-NMR (CDCl 3) d: 8.60 (d, 1 H), 7.69 (d, 1 H), 7.52 (d, 1 H), 6.62 (d, 1 H), 4.29 (m, 2 H), 4.14 ( m, 1 H), 3.04 (m, 1 H), 2.88 (m, 2H), 2.33 (m, 1 H), 2.20 (m, 1 H), 1.98 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 94 (11, 21 >?, 5) -3-Decladoinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl-f3- (2-pyridinyl) H-imidazol-1-yl) -propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 90 (0.025 g) in anhydrous acetonitrile (2 mL) was stirred at 50 ° C for 6 hours, and then at room temperature overnight under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.150 mL) and acetic acid (0.006 mL) were added. After 72 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over Na 2 SO and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 90 \ 10), to give the title compound (0.014 g). 1 H-NMR (CDCl 3) d: 8.27 (d, 1 H), 7.59 (d, 1 H), 7.19 (m, 1 H), 7.16 (m, 1 H), 4.30-4.10 (m, 3 H), 3.15 (m, 2H), 2.96 (m, 1 H), 2.31 (m, 1 H), 2.00-1.82 (m, 2H), 1.09 (d, 3 H).

EXAMPLE 95 f11 ^ 21 ^) -3-Decladoinosyl-11,12-dideoxy-6-0-metit-3-oxo-12,11-roxycarbonyl- (3- (4-quinolin-2-yl-1H-pyrazole- 1-SI) -propylamine) -methylene-1-erythromycin A A solution of Example 7 (0.050 g) and intermediate 91 (0.032 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1 mL), and then sodium cyanoborohydride (1M in THF) was added., 0.037 mL) and acetic acid (0.004 mL). After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 98 \ 2 to 94 \ 6) and by preparative TLC (DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the title compound (0.018 g ). 1 H-NMR (CDCl 3) d: 8.20 (s, 1 H), 8.14 (s, 1 H), 8.12 (d, 1 H), 8.04 (d, 1 H), 7.76 (d, 1 H), 7.67 (t, 1 H), 7.66 (d, 1H), 7.45 (t 1H), 5.68 (dd, 1H), 4.31 (m, 3 H), 4.26 (d, 1H), 4.15 (s, 1H), 3.86 (q, 1H), 3.56 (m, 1H), 3.18 (dd, 1H), 3.11 (m, 1H), 3.05 (m, 1H), 2.95 ÷ 2.80 (m, 2H), 2.70 (s, 3 H), 2.58 (m, 1H) , 2.46 (m, 1H), 2.35 (s, 1H), 2.27 (s, 6 H), 2.14 (m, 1H), 2.06 (m, 1H), 1.96 (m, 1H), 1.80 (m, 1H) , 1.74 (m, 1H), 1.70 (m, 1H), 1.65 (m, 1H), 1.50 (s, 3 H), 1.40 (d, 3 H), 1.34 (s, 3 H), 1.32 (d, 3 H), 1.25 (m, 1 H), 1.24 (d, 3 H), 1.16 (d, 3 H), 1.10 (d, 3 H), 0.90 (t, 3 H).

EXAMPLE 96 (11 £ 21>, 5 -3-Dec »adinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl-f3- (4-quinoline ^ Hl-1 Hp! Razol-1-yl) -proprilam8no) -methylene1- erythromycin A A solution of Example 7 (0.050 g) and intermediate 92 (0.034 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous eOH (1 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (using: DCMWleOH from 98 \ 2 to 94 \ 6), to give the title compound (0.020 g). 1 H-NMR (CDCl 3) d: 8.89 (d, 1 H), 8.25 (d, 1 H), 8.14 (d, 1 H), 7.87. (s, 1H), 7.84 (s, 1 H), 7.73 (m, 1 H), 7.59 (m, 1 H), 7.42 (d, H), 5.63 (dd, H), .37 (m, 2H ), 4.30 (d, 1 H), 4.24 (d, 1 H), 4.16 (s, 1 H), 3.85 (q, 1 H), 3.55 (m, 1 H), 3.18 (dd, 1 H), 3.10 (m, 1 H), 3.04 (m, 1 H), 2.94 (m, 2H), 2.70 (s, 3 H), 2.58 (m, 1 H), 2.45 (m, 1 H), 2.34 (s) , 1 H), 2.27 (s, 6 H), 2.19 (m, 1 H), 2.05 (m, 1 H), 1.88 (m, 1 H), 1.80 (dd, H), 1.73 (m, 1 H ), 1.67 (m, 1 H), 1.56 (m, 1 H), 1.49 (s, 3 H), 1.38 (d, 3 H), 1.33 (s, 3 H), 1.32 (d, 3 H), 1.25 (m, 1 H), 1.24 (d, 3 H), 1.15 (d, 3 H), 1 .10 (d, 3 H), 0.83 (t, 3 H).

EXAMPLE 97 (1 £ 21 and?, 5) -3-Decladoinosyl-11.12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (4-quinoxalin-2-M-1H- pyrazol-1-yl) -propHamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 93 (0.030 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 98 \ 2 to 94 \ 6) and by preparative TLC (DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the title compound (0.006 g ). 1 H-NMR (CDCl 3) d: 9.10 (s, 1 H), 8.28 (s, 1 H), 8.22 (s, 1 H), 8.03 (m, 2 H), 7.73 (t, 1 H), 7.66 ( t, 1 H), 5.63 (dd, 1 H), 4.35 (m, 2H), 4.30 (d, 1H), 4.26 (d, 1 H), 4.15 (m, 1 H), 3.87 (q, 1 H ), 3.55 (m, 1 H), 3.17 (m, 1 H), 3.11 (m, 1 H), 3.05 (m, 1 H), 3.00 ÷ 2.80 (m, 2 H), 2.71 (s, 3 H) , 2.60 (m, 1 H), 2.46 (m, 1H), 2.35 (m, 1 H), 2.27 (s, 6 H), 2.15 (m, 1 H), 2.06 (m, 1 H), 1.96 ( m, 1 H), 1.80 (m, 1H), 1.74 (m, 1 H), 1.68 (m, 1 H), 1.60 (m, 1H), 1.50 (s, 3 H), 1.40 (d, 3 H), 1.34 (s, 3 H), 1.32 (d, 3 H), 1.30 (m, 1 H), 1.24 (d, 3 H), 1.16 (d, 3 H), 1.10 (d, 3 H) , 0.90 (t, 3 H).

EXAMPLE 98 (1S21 / ?, 5) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11- [oxycarbonyl- (3-thien-3-ylpropylamine) -rnetylene 1- erythromycin A A solution of Example 7 (0.042 g) and intermediate 94 (0.025 g) in anhydrous acetonitrile (2 mL) was stirred at 50 ° C for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 in THF, 0.035 mL) and acetic acid (0.004 mL) were added. After 18 hours at room temperature, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMUvleOH from 100 \ 0 to 98 \ 2), to give the title compound (0.012 g). 1 H-NMR (CDCl 3) d: 7.21 (m, 1 H), 6.94 (m, 2 H), 4.13 (m, 1 H), 3.03 (m, 1 H), 2.91 (m, 1 H), 2.83 ( m, 1 H), 2.80-2.60 (m, 2H), 2.31 (m, 1 H), 1.80 (m, 2H), 1.09 (d, 3 H).

EXAMPLE 99 (11 £ 21) -3-Pecladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11-phyclocarbonyl-3-f5- (3-methyl-pyrazin-2-yl) -pyrazol -1-in-propylamino) -metholenol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 95 (0.037 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.075 mL) and acetic acid (0.009 mL) were added. After 20 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 94 \ 6), to give the title compound (0.018 g). 1 H-NMR (CDCl 3) d: 8.44 (d, 1 H), 8.36 (d, 1 H), 7.54 (d, 1 H), 6.82 (d, 1 H), 4.40-4.20 (m, 2H), 4.14 (m, 1 H), 3.04 (m, 1 H), 2.90 (s, 3 H), 2.89 (m, 2 H), 2.33 (m, 1 H), 2.15 (m, 1 H), 2.05 (m , 1 H), 1 .10 (d, 3 H).

EXAMPLE 100 (11 £ 21?, 5) -3-DecladoinsH-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (3-r2- (methylthio) -1H-benzimidazole -1-l, l-propylamino) -methylene-lolithromycin A A solution of Example 7 (0.050 g) and intermediate 96 (0.037 g) in anhydrous acetoniiryl (1 mL) was stirred at room temperature for 3 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.075 mL) and acetic acid (0.009 mL) were added. After 20 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWIeOH of 98 \ 2), to give the title compound (0.020 g). 1 H-NMR (CDCl 3) d: 7.66 (m, 1 H), 7.40 (m, 1 H), 7.35 (m, 1 H), 7.20 (m, 1 H), 4.15 (m, 1 H), 4.25 (m, 1 H), 4.13 (m, 1 H), 3.05 (m, 1 H), 2.95 (m, 2H), 2.79 (m, 2H), 2.36 (m, 1 H), 2.00 (m, 1 H), 1.86 (m, 1 H), 1 .10 (d, 3 H).

EXAMPLE 101 (11 21 >?,) -3-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl-f3-f3-f4-chlorophenH) -1H ^ »r -5-ill ^ ropHamino) -metHeno1- erythromycin A A solution of Example 7 (0.040 g) and intermediate 97 (0.035 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 12 hours, and then heated at 50 ° C for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1 M in THF, 0.030 mL) and acetic acid (0.004 mL) were added. After 12 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over a2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 97 \ 3), to give the title compound (0.017 g). 1 H-NMR (CDCl 3) d: 7.73 (d, 2H), 7.35 (d, 2H), 6.35 (s, 1 H), 4.15 (m, 1 H), 2.93 (m, 2H), 2.82 (m, 1 H), 2.34 (m, 1 H), 1.88 (m, 1 H).

EXAMPLE 102 (11 £ 21 / ?, Sl-3-Decladinosyl-11, 12-d-Deoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl-f3-f6-fmethyl) -7H- purin-7-n-propylamino) -methylene1- erythromycin A A solution of Example 7 (0.040 g) and intermediate 98 (0.042 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 3 hours, and then heated at 50 ° C for 3 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1 M in THF, 0.060 mL) and acetic acid (0.008 mL) were added. After 6 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO3 (2x3 mL). The organic phase was dried over a2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DC \ MeOH from 100 \ 0 to 98 \ 2), to give the title compound (0.005 g). 1 H-NMR (CDCl 3) d: 8.85 (m, 1 H), 8.25 (s, 1 H), 4.63 (m, 1 H), 4.45 (m, 1 H), 4.15 (m, 1 H), 2.97 (m, 2H), 2.76 (s, 3 H), 2.33 (m, 1 H), 2.0 ÷ 2.2 (m, 2H).

EXAMPLE 103 (11 5 *, 21?.) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (3- (6-methoxy) 7H-purin-7-in-propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and Intermediate 99 (0.031 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature overnight under a nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1 M in THF, 0.074 mL) and acetic acid (0.010 mL) were added. After 4 hours, the solvent was removed under reduced pressure, the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 00 \ 0 to 97 \ 3), to give the title compound (0.015 g). i H-NMR (CDCl 3) 5: 8.54 (s, 1 H), 8.07 (s, 1 H), 5.58 (dd, 1 H), 4.37 (t, 2 H), 4.31 (d, 1 H), 4.25 ( d, 1 H), 4.19 (s, 3 H), 4.13 (bs, 1 H), 3.86 (q, 1 H), 3.55 (m, 1 H), 3.20 (m, 1 H), 3.10 (m, 1 H), 3.04 (m, 1 H), 2.89 (bm, 2H), 2.70 (s, 3 H), 2.59 (m, 1 H), 2.48 (bm, 1 H), 2.34 (s, 1 H) , 2.29 (s, 6 H), 2.12 (m, 1 H), 2.04 (m, 1 H), 1.95 (m, 1 H), 1.85-1.48 (m, 5 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.34 (s, 3 H), 1.32 (d, 3 H), 1.25 (d + m, 3 H + 1 H), 1.16 (d, 3 H), 1.10 (d) , 3 H), 0.89 (t, 3 H).

EXAMPLE 104 (11 21? R «S) -3-Decladinosyl-11.12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (6-methoxy-2-oxo-1,3 -benzoxazole-3 (2H) -l) -propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.043 g) and intermediate 100 (0.025 g) in anhydrous acetonitrile (2 mL) was stirred at room temperature for 30 minutes, and then heated at 50 ° C for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.030 mL) and acetic acid (0.005 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 97 \ 3), to give the title compound (0.007 g). 1 H-NMR (CDCl 3) d: 7.05 (d, 1 H), 6.82 (d, 1 H), 6.47 (d, 1 H), 4.13 (s, 1 H), 3.87 (m, 2 H), 3.81 (d. s, 3 H), 3.04 (m, 1 H), 2.97-2.92 (m, 2H), 2.34 (m, 1 H), 1.96 (m, 1 H), 1.80 (m, 1 H), 1.09 (d , 3 H).

EXAMPLE 105 ni ^ 21 > ?,) -3-ecladinosyl-11,12-d-cholesoxy-6-0-metH-3-oxo-12,11-foxycarbonyl- (3- (1H-pyrrolor-2,3-b1-pyridin-1-yl) -propylamino) -methieno1- erythromycin A A solution of Example 7 (0.050 g) and intermediate 101 (0.042 g) in anhydrous acetonitrile (1.5 mL) was stirred at room temperature for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (1.5 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.005 mL) were added. After 8 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH4OH 95 \ 5 \ 0.5), to give the title compound (0.006 g). 1 H-NMR (CDC13) d: 8.30 (dd, 1H), 7.87 (dd, 1 H), 7.30 (d, 1 H), 7.03 (dd, 1 H), 6.43 (d, 1 H), 5.71 (d. dd, 1 H), 4.44 ÷ 4.36 (m, 2 H), 4.32 (d, 1 H), 4.25 (d, 1 H), 4.13 (s, 1 H), 3.85 (q, 1 H), 3.55 (m , 1 H), 3.22 (dd, 1 H), 3.11 (m, 1 H), 3.04 (m, 1 H), 2.90 ÷ 2.78 (m, 2H), 2.70 (s, 3 H), 2.62 ÷ 2.50 ( m, 2H), 2.35 (s, 1 H), 2.32 (s, 6 H), 2.06 (m, 1 H), 2.00 (m, 1 H), 1.95 (m, 1 H), 1.80 ÷ 1.68 (m , 3 H), 1.58 (m, 1 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.33 (s, 3 H), 1.32 (d, 3 H), 1.25 (m, 1 H), 1.25 (d, 3 H), 1.15 (d, 3 H), 1.10 (d, 3 H), 0.89 (t, 3 H).

EXAMPLE 106 (1: 21 / ?,) -3-We declare H-11,12-dfdeoxy-6-0-metH-3-oxo-12,11- [oxycarbonyl- (2-f1,3-dioxo-1, 3-dihydro-2H-isoindol-2-yl) -ethylamino) - methyleneol-erythromycin A To a solution of Example 13 (0.232 g) in anhydrous DMF (5 mL), 2 - [(1,3-thiazol-2-ylamino) carbonyl] benzoic acid (0.097 g), benzotriazole-1-hexafluorophosphate was added. iloxy) tripyrrolidinophosphonium (0.186 g) and DI PEA (0.120 mL), and the resulting mixture was stirred overnight at room temperature. It was diluted with DC (0 mL) and washed with an aqueous solution of NaHCC > 3 to 5% (2x5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in DCM (5 mL), loaded into SCX cartridges (5 g, loading 0.75 mmol g, prewashed with 50 mL of MeOH), washed with MeOH (50 mL), and then the product was eluted with NH3 (0.25M solution in MeOH, 60 mL), followed by MeOH (10 mL). Evaporation of the solvent gave the title compound (0.170 g). 1 H-NMR (CDCl 3) d: 7.80 (m, 2H), 7.67 (m, 2H), 5.53 (dd, 1 H), 4.30 (d, 1 H), 4.24 (d, 1 H), 4.17 (s) , 1 H), 3.84 (m, 2H), 3.74 (m, 1 H), 3.55 (m, 1 H), 3.20-3.15 (m, 2H), 3.12-2.88 (m, 3 H), 2.63 (s) , 3 H), 2.54 (m, 1 H), 2.47 (m, 1 H), 2.30 (m, 1 H), 2.27 (s, 6 H), 1.86 (m, 1 H), 1.75-1.65 (m , 3 H), 1.48 (m, 1 H), 1.43 (s, 3 H), 1.29 (s, 3 H), 1.28-1.24 (m, 2 * 3H + 1 H), 1.19 (d, 3 H) , 1.12 (d, 3 H), 1.06 (d, 3 H), 0.73 (t, 3 H).

EXAMPLE 107 (11 £ 21 /?,5)-3-Pecladinosil-11.12-didesoxy-6- Q -methyl 3 -oxo-12,11-roxycarbonyl- (3-r 3 - (2,4-dimethyl-1, 3-thiazoyl-5-yl) -1 H-pyrazol-1-??-propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 102 (0.042 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 6 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.070 mL) and acetic acid (0.009 mL) were added. After 20 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH of 98 \ 2), to give the title compound (0.016 g). 1 H-NMR (CDCl 3) d: 7.49 (d, 1 H), 6.36 (d, 1 H), 5.62 (d, 1 H), 4.31 (d, 1 H), 4.25 (d, 1 H), 4.23 (m, 2H), 4.13 (s, 1 H), 3.85 (q, 1 H), 3.56 (m, 1 H), 3.19 (m, 1 H), 3.10 (m, 1 H), 3.03 (m, 1 H), 2.92 ÷ 2.82 (m, 2H), 2.69 (s, 3 H), 2.66 (s, 3 H), 2.58 (m, 1 H), 2.55 (s, 3 H), 2.47 (m, 1 H), 2.33 (s, 1 H), 2.28 (s, 6 H), 2.08 (m, 1 H), 1.98 (m, 1 H), 1.94 (m, 1 H), 1.80 (m, 1 H) , 1.76 ÷ 1.66 (m, 2H), 1.62 ÷ 1.50 (m, 1 H), 1.49 (s, 3 H), 1 .39 (d, 3 H), .34 (s, 3 H) , 1.32 (d, 3 H), 1.25 (m, 1 H), 1.25 (d, 3 H), 1.15 (d, 3 H), 1 .10 (d, 3 H), 0.88 (t, 3 H) .

EXAMPLE 108 (11: 21?,) -3-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-oxocarbonyl-f3-f1 H-imidazof4,5- ^ pyrid n-1-yl) -propylamino) -methyllenol-erythromycin A and EXAMPLE 109 (1: 21 7,) -3-Decladoinosi 1.12-d-deoxy-6-0-met8l-3-oxo-12.11-dioxycarbonyl - (3- (3 H-imidazor4,5-j-pyridin-3-yl) -propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 103 (0.034 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SC > 4 and concentrated under reduced pressure. The crude material was purified by preparative TLC (DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the title compound 108 (0.008 g) and the title compound 109 (0.004 g). 1 H-NMR (CDCl 3) d (example 108): 9.11 (s, 1 H), 8.44 (d, 1 H), 8.08 (s, 1 H), 7.47 (d, 1 H), 4.41 (m, 1 H), 4.28 (m , 1H), 4.14 (m, 1H), 3.05 (m, 1H), 3.00-2.90 (m, 2H), 2.31 (m, 1H), 2.08 (m, 1H), 1.95 (m, 1H), 1.09 ( d, 3 H). 1 H NMR (CDCl 3) d (example 109): 8.90 (s, 1 H), 8.45 (d, 1 H), 8.16 (s, 1 H), 7.70 (d, 1 H), 4.48 (m, 1 H), 4.37 (m, 1H), 4.15 (bs, 1H), 3.08 (m, 1H), 2.95 (m, 1H), 2.33 (m, 1H), 2.14 (m, 1H), 2.04 (m, 1H), 1.09 (d, 3 H).

EXAMPLE 110 fli ^ IP ^ -a-Decladinosyl-II.IZ-dideoxy-eO-methyl-S-oxo-i. L-roxycarbonyl- (3- (1H-benzyldazol-1-yl) - propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 104 (0.025 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 94 \ 6), to give the title compound (0.021 g).

? ? -NRM (CDCI3) d: 8.00 (s, 1 H), 7.80 (d, 1 H), 7.48 (d, 1 H), 7.40-7.20 (m, 2H), 4.38 (m, 1 H), 4.24 (m, 1 H), 4.10 (m, 1 H), 3.05 (m, 1 H), 3.03 (m, 1 H), 2.98 (m, 1 H), 2.32 (m, 1 H), 2.02 (m , 1 H), 1 .93 (m, 1 H), 1 .09 (d, 3 H).

EXAMPLE 111 (11.9.21 / ?, 5) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (3- (3 H-imidazor4,5- ^ pyridin-3-yl) -propylamino) -methyleneol-erythromycin A A solution of example 7 (0.050 g) and intermediate 105 (0.034 g) in anhydrous acetonitrile (1 mL), was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous NaHCO3 solution (2x3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 94 \ 6) and by preparative TLC (eluting with: DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the title compound ( 0.004 g). 1 H-NMR (CDCIS) d: 8.39 (dd, 1 H), 8.21 (s, 1 H), 8.05 (dd, 1 H), 7.22 (dd, 1 H), 4.43 (t, 2H), 4.15 ( m, 1 H), 3.04 (m, 1 H), 2.32 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 112 M 1: 21?, "S) -3-We declare l-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (quinoxalin-2-ylsulfanyl) -propylamino) -methylene1- erythromycin A A solution of intermediate 106 (0.080 g) in acetonitrile (3 mL), and an aqueous solution of HCI at 2N (2 mL), were heated at 40 ° C for 1 hour. The reaction mixture was cooled to room temperature, and then added dropwise to a solution of Example 7 (0.090 g) dissolved in anhydrous acetonitrile (3 mL), maintaining the pH of the solution on the scale of 6-7 by the addition of saturated aqueous solution of NaHCO3. The solution was stirred at room temperature overnight. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.200 mL). The reaction mixture was stirred for 5 hours at room temperature. After evaporating the solvent, saturated aqueous NaHCO3 solution (10 mL) was added, and the product was extracted with DCM (4x15 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in MeOH (4 mL) and stirred overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with DCM \ MeOH from 98 \ 2 to 96 \ 4), giving the title compound (0.050 g). m \ z ([H] +) = 829. 1 H-NMR (CDCIs) d: 8.57 (s, 1 H), 7.99 (d, 1 H), 7.96 (d, 1 H), 7.69 (t, 1 H ), 7.60 (t, 1 H), 5.71 (dd, 1 H), 4.32 (d, 1 H), 4.25 (m, 1 H), 4.17 (m, 1 H), 3.84 (q, 1 H), 3.57 (m, 1 H), 3.25 (m, 1 H), 3.50-2.90 (m, 4 H), 3.20-2.90 (m, 4 H), 2.69 (s, 3 H), 2.58 (m, 1 H) , 2.37 (s, 6 H), 2.34 (m, 1 H), 2.10-1.85 (m, 3 H), 1.80-1.40 (m, 4 H), 1.49 (s, 3 H), 1.37 (d, 3 H), 1.31 (d, 3 H), 1.31 (s, 3 H), 1.28 (m, 1 H), 1.25 (d, 3 H), 1 .15 (d, 3 H), 1.10 (d, 3 H), 0.85 (t, 3 H).

EXAMPLE 113 (l ^ l ^ -S-Decladinosyl-Hia-diodeoxy-SO-ineti-a-oxo-^.-L-oxoxycarbonyl- (3- (4-phenyl-H-imidazol-1-yl-propyl) no) -methyl-T-erythromycin A A solution of Example 7 (0.050 g) and intermediate 107 (0.027 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na 2 SO and concentrated under reduced pressure. The crude material was purified by preparative TLC (eluting with: DCM \ MeOH \ NH4OH 90 \ 9 \ 0.5), to give the title compound (0.012 g). 1 H NMR (CDCl 3) d: 7.79 (d, 2 H), 7.56 (m, 1 H), 7.36 (m, 2 H), 7.29 (d, 1 H), 7.25 (m, 1 H), 4.32 (m , 1 H), 4.15 (m, 1 H), 4.04 (m, 1 H), 3.05 (m, 1 H), 3.05-2.95 (m, 2H), 2.33 (m, H), 1.98 (m, 1 H), 1.80 (m, 1 H), 1.09 (d, 3 H).

EXAMPLE 114 (11, 21 and?, 5) -3-Dec) adinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxScarbonyl- (2- (4-pyridine) -yl-1H-imidazol-1-n-ethylamino) -methylene-1-erythromycin A A solution of intermediate 108 (0.060 g) in acetonitrile (1.5 mL) and an aqueous solution of 3M HCl (1.5 mL) was stirred at 70 ° C for 14 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 7 (0.030 g) dissolved in anhydrous acetonitrile (1 mL), keeping the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCO 3. The solution was stirred at room temperature for 4 hours. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.150 mL). The reaction mixture was stirred for 72 hours at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCO 3 (3 mL) was added, and the mixture was extracted with DCM (3x5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with DCMWleOH from 100 \ 0 to 97 \ 3) and by preparative TLC (eluting with: DCMWleOH 90? 10), to give the title compound (0.004 g). 1 H-NMR (CDCl 3) d: 8.57 (d, 2H), 7.72 (d, 2H), 7.71 (m, 1 H), 7.60 (m, 1 H), 5.63 (dd, 1 H), 4.27 (d , 1 H), 4.19 (s, 1 H), 4.18 (d, 1 H), 4.12 (m, 2 H), 3.85 (q, 1 H), 3.55 (m, 1 H), 3.32 (m, 1 H ), 3.24 (m, 1 H), 3.16 (dd, 1 H), 3.05 (m, 1 H), 3.03 (m, 1 H), 2.56 (m, 1 H), 2.44 (m, 1 H), 2.41 (s, 3 H), 2.27 (s, 1 H), 2.26 (s, 6 H), 1.85 (m, 1 H), 1.78 (m, 1 H), 1.70 ÷ 1.63 (m, 2H), 1.55 (m, 1 H), 1.48 (s, 3 H), 1.41 (d, 3 H), 1.31 (d, 3 H), 1.24 (m, 1 H), 1.24 (d, 3 H), 1.23 (s) , 3 H), 1.14 (d, 3 H), 1.09 (d, 3 H), 0.81 (t, 3 H).

EXAMPLE 115 (11 21?) -3-Decladinosll-11,12-d-Desoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (2- (qu.). Noxalin-2-ylsulfanH ) ^ t¡lamino) -methylene1 ^ ritromycin A A solution of intermediate 109 (0.067 g) in acetonitrile (3 mL), and an aqueous solution of HCI at 2N (2 mL), were stirred overnight. Then, the reaction mixture was added dropwise to a solution of Example 7 (0.090 g) dissolved in anhydrous acetonitrile (3 mL), maintaining the pH of the solution on a scale of 6-7 by the addition of saturated aqueous solution. of NaHCC > 3. The reaction mixture was stirred at room temperature for 3 hours. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.200 mL). The reaction mixture was stirred for 5 hours at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCO3 (10 mL) was added, and the mixture was extracted with DCM (4x15 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in MeOH (4 mL) and stirred overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with DCM \ MeOH from 98 \ 2 to 96 \ 4), to give the title compound (0.076 g). m \ z ([MH] +) = 815. iH-NMR (CDCI3) d: 8.55 (s, 1 H), 7.99 (d, 1 H), 7.93 (d, H), 7.68 (t, 1 H) , 7.60 (t, 1 H), 5.68 (dd, 1 H), 4.32 (d, 1 H), 4.26 (d, 1 H), 4.21 (m, 1 H), 3.83 (q, 1 H), 3.62 -3.48 (m, 3 H), 3.23 (m, 2H), 3.19 (dd, 1 H), 3.10 (m, 1 H), 3.04 (m, 1 H), 2.74 (s, 3 H), 2.58 ( m, 1 H), 2.48 (m, 1 H), 2.35 (s, 1 H), 2.29 (s, 6 H), 1.91 (m, 1 H), 1.80-1.67 (m, 3 H), 1.55 ( m, 1 H), 1.49 (s, 3 H), 1.35 (d, 3 H), 1.30 (d, 3 H), 1.34 (s, 3 H), 1.26 (m, 1 H), 1.25 ( d, 3 H), 1.14 (d, 3 H), 1.09 (d, 3 H), 0.86 (t, 3 H).

EXAMPLE 116 (11: 21 → 5) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11- [oxycarbonyl- (3- (4- (thiophen-2-yl) ) -imidazol-1-yl) -propylamine) -methi [ene-erythromycin A] A solution of Example 6 (0.040 g) and intermediate 110 (0.033 g) in anhydrous acetonitide (1.5 mL) was stirred at room temperature for 12 hours. After evaporating the solvent, the residue was dissolved in anhydrous MeOH (1.5 mL), and sodium cyanoborohydride (1 M in THF, 0.030 mL) and acetic acid (0.004 mL) were added. The reaction mixture was stirred for 12 hours. The solvent was evaporated under vacuum, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 2 mL). The organic layer was dried over Na2SC > and concentrated under vacuum. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH 100 \ 0, 98 \ 2, 97 \ 3) to give the title compound (0.025 g). H-NMR (CDCl 3) d: 7.52 (d, 1 H), 7.18 (d, 1 H), 7.27 (m, 1 H), 7.16 (d, 1 H), 7.02 (dd, 1 H), 5.58 ( dd, 1 H), 4.31 (d, 1 H), 4.25 (d, 1 H), 4.14 (m, 1 H), 4.12 (m, 1 H), 4.02 (m, 1 H), 3.86 (q, 1 H), 3.56 (m, 1 H), 3.20 (m, 1 H), 3.10 (m, 1 H), 3.04 (m, 1 H), 2.93 (m, 2 H), 2.68 (s, 3 H) , 2.60 (m, 1 H), 2.50 (m, 1 H), 2.32 (m; 1 H), 2.30 (s, 6 H), 2.05-1.85 (m, 3 H), 1.80 (m, 1 H), 1.70 (m, 2H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1.39 (d, 3 H), 1.34 (s, 3 H), 1.32 (d, 3 H), 1.25 (d + m, 3H + 1 H), 1.16 (d, 3 H), 1.10 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 117 (11 «S21) -3-Decladoinosyl-, 12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (3- (4- (thiophen-2-yl) -imidazol-1-yl) ^ ropylamino) -methylene1- erythromycin A A solution of Example 7 (0.750 g) and intermediate 110 (0.300 g) in anhydrous acetonitrile (15 mL) was stirred at room temperature for 12 hours. After evaporating the solvent, the residue was dissolved in anhydrous MeOH (15 mL), and sodium cyanoborohydride (1 M in THF, 0.728 mL) and acetic acid (0.084 mL) were added. The mixture was stirred overnight at room temperature. The solvent was evaporated under vacuum, and the crude material was dissolved in DCM (50 mL) and washed with saturated aqueous NaHCO3 solution (2x20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 95 \ 5 to 90 \ 10), to give the title compound (0.872 g, 95% pure isomer (21 5) by NMR analysis) . 1 H-NMR (CDCl 3) d: 7.52 (d, 1 H), 7.18 (d, 1 H), 7.27 (m, H), 7.16 (d, 1 H), 7.02 (dd, 1 H), 5.58 (d. dd, 1 H), 4.31 (d, 1 H), 4.25 (d, 1 H), 4.14 (m, 1 H), 4.12 (m, 1 H), 4.02 (m, 1 H), 3.86 (q, 1 H), 3.56 (m, 1 H), 3.20 (m, 1 H), 3.10 (m, H), 3.04 (m, 1 H), 2.93 (m, 2H), 2.68 (s, -OCH3), 2.60 (m, 1 H), 2.50 (m, 1 H), 2.32 (m, 1 H), 2.30 (s, N (CH3) 2), 2.05-1.85 (m, 3 H), 1.80 (m, 1 H), 1.70 (m, 2H), 1.60 (m, 1 H), 1.49 (s, 3 H), 1 .39 (d, 3 H), 1.34 (s, 3 H), 1.32 (d, 3 H) ), 1.25 (d + m, 3H + 1H), 1.16 (d, 3 H), 1.10 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 118 (11 £ 21 /? 5) -3-Decladinosyl-11, 2-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (6-methyl-2-oxo- 1,3-benzoxazol-3 (2H) -yl) -propylamino) -methyleneol-erythromycin A A solution of Example 7 (0.050 g) and intermediate 111 (0.035 g) in anhydrous acetonitrile (2 mL) was stirred at 50 ° C for 6 hours. After cooling to room temperature, the solvent was evaporated, the residue was dissolved in anhydrous MeOH (2 mL), and sodium cyanoborohydride (1 M in THF, 0.140 mL) and acetic acid (0.010 mL) were added. The mixture was stirred overnight at room temperature. The solvent was evaporated under vacuum, and the residue was dissolved in DCM (50 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with: DCM WleOH from 100 \ 0 to 95 \ 5) to give the title compound (0.020 g). H-NMR (CDCl 3) d: 7.20-6.80 (m, 3 H), 5.66 (dd, 1 H), 4.38 (d, 1 H), 4.26 (d, 1 H), 4.11 (s, 1 H), 3.88 (m, 3 H), 3.67 (m, 1 H), 3.41 (m, 1 H), 3.20-2.85 (m, 5 H), 2.71 (s, 3 H), 2.70 (bs, 6 H), 2.59 (m, 1 H), 2.41-2.35 (m, 1 H + 3 H), 2.00-1.55 (m, 7 H), 1.50 (s, 3 H), 1.39 (d, 1 H + 3 H), 1 .32-1.27 (m, 3 * 3 H), 1.18 (d, 3 H), 1.10 (d, 3 H), 0.88 ( t, 3 H).

EXAMPLE 119 (11 21/7,) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (2-pyridin-1-yl-1H-imidazole -1-yl) -atylamino) -metHeno1- erythromycin A A solution of intermediate 112 (0.060 g) in acetonitrile (3 mL), and an aqueous solution of HC! at 3M (3 mL), were stirred at 80 ° C for 3 days. The reaction mixture was allowed to reach room temperature, and then it was added dropwise to a solution of Example 7 (0.050 g) dissolved in anhydrous acetonitrile (2 mL), keeping the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCO 3. The solution was stirred at room temperature for 24 hours. Acetic acid was added to the mixture until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.070 mL). The reaction mixture was stirred for 16 hours at room temperature. After evaporating the solvent, saturated aqueous NaHCOe solution (3 mL) was added, and the product was extracted with DC (3x5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was dissolved in MeOH (1 mL) and stirred overnight. After evaporating the solvent, the compound was purified by flash chromatography (eluting with DCM \ MeOH from 100 \ 0 to 97 \ 3), to give the title compound (0.004 g). m \ z ([MH] +) = 798.

EXAMPLE 120 (115: 21 >?, "A-3-Decladinosil-11.12-d-deoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (3-r3-f5-cyano-3 , 4-dimethylol-2-yl) -1 H-1, 2,4-triazol-1-yl-propylamino) -methylene-erythromycin A A solution of Example 7 (0.050 g) and the intermediate 113 (0.046 g) in anhydrous acetonitrile (2 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the residue was dissolved in anhydrous eOH (2 mL), and then sodium cyanoborohydride (1M in THF, 0.070 mL) and acetic acid (0.009 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100? 0 to 94? 6), to give the title compound (0.001 g). I NR (CDCI3) d: 8.23 (s, 1 H), 5.51 (dd, 1 H), 4.38 ÷ 4.20 (m, 4 H), 4.12 (s, 1 H), 3.86 (m, 1 H), 3.55 (m, 1 H), 3.18 (dd, 1 H), 3.12 ÷ 3.00 (m, 2H), 2.98 ÷ 2.84 (m, 2H), 2.68 (s, 3 H), 2.58 (m, 1 H), 2.52 (s, 3 H), 2.44 (m, 1 H), 2.37 (s, 3 H), 2.32 (s, 1 H), 2.27 (s, 6 H), 2.12 (m, 1 H), 2.02 ( m, 1H), 1.92 (m, 1H), 1.81 (m, 1H), 1.74 ÷ 1.63 (m, 2H), 1.55 (m, 1H), 1.49 (s, 3 H), 1.38 (d, 3 H) , 1.33 (s, 3 H), 1.32 (d, 3 H), 1.25 (m, 1H), 1.25 (d, 3 H), 1.15 (d, 3 H), 1.09 (d, 3 H), 0.88 ( t, 3 H).

EXAMPLE 121 f11, 21 g) -3 ecladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (3- (quinolin-3-yl) -propylamino) -methylene ^ ritromycin A A solution of example 7 (0.050 g) and intermediary 114 (0.041 g) in anhydrous acetonitrile (2 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the residue was dissolved in anhydrous eOH (2 mL), and then sodium cyanoborohydride (1M in THF, 0.070 mL) and acetic acid (0.009 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 3 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWIeOH from 100 \ 0 to 94 \ 6), to give the title compound (0.009 g). 1 H-NMR (CDCl 3) d: 8.79 (d, 1 H), 8.07 (d, 1 H), 7.97 (d, 1 H), 7.79 (d, 1 H), 7.65 (t, 1 H), 7.52 (t, 1 H), 5.74 (dd, 1H), 4.32 (d, 1H), 4.25 (d, 1H), 4.17 (s, 1H), 3.85 (q, 1H), 3.55 (m, ÍH), 3.22 (m, 1H), 3.11 (m, 1H), 3.04 (m, 1H), 3.02 ÷ 2.78 (m, 4 H), 2.69 (s, 3 H), 2.99 (m, 1 H), 2.52 (m, 1 H), 2.34 (s) , 1 H), 2.32 (s, 6 H), 1.94 (m, 1 H), 1.89 (m, 2H), 1.88 ÷ 1.66 (m, 3 H), 1 .62 ÷ 1.50 (m, 1 H), 1.49 (s, 3 H), 1 .39 (d, 3 H), 1 .32 (m, 6 H), 1 .25 (m, 1 H), 1 .25 (d, 3 H) ), 1 .16 (d, 3 H), 1 .10 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 122 (11"LÁ-S-DecladinosiM 1.12-dideoxy-6-0-methyl-3-oxo-2, -roxycarbonyl- (3-r4- (3-nitrophenyl) -1 H-! Midazole-1-yl -propylamino) -methylene] - erythromycin A A solution of Example 7 (0.050 g) and intermediate 115 (0.026 g) in anhydrous acetonitrile (1 mL) was stirred at room temperature for 18 hours under nitrogen atmosphere. The solvent was evaporated under reduced pressure, the crude material was dissolved in anhydrous MeOH (2 mL), and then sodium cyanoborohydride (1 M in THF, 0.037 mL) and acetic acid (0.004 mL) were added. After 18 hours, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (5 mL) and washed with saturated aqueous solution of NaHCC > 3 (2x3 mL). The organic phase was dried over Na2SC > 4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DC WleOH from 100 \ 0 to 94 \ 6), to give the title compound (0.007 g). 1 H-NMR (CDCIS) d: 8.62 (t, 1 H), 8.17 (d, 1 H), 8.05 (d, 1 H), 7.60 (d, 1 H), 4.1 5 (m, 2 H), 4.09 (m, 1 H), 4.05 (m, 1 H), 3.02 (m, 1 H), 3.04-2.92 (m, 2 H), 2.33 (m, 1 H), 2.05 (m, 1 H), 1. 98 (m, 1 H), 1 .12 (d, 3 H).

EXAMPLE 123 (11 .9.21 y?, S) -3-Decladinosil-11, 12-d-deoxy-6-0-methy1-3-oxo-12.11-hydroxycarbonH- (r2- (2,3- dihydro-1,4-benzodith erythromycin A To a solution of Example 7 (0.100 g) in anhydrous acetonitrile, intermediate 117 (0.066 g) was added in portions at room temperature under nitrogen atmosphere. After stirring overnight, the solvent was removed under reduced pressure, the residue was dissolved in MeOH (2.5 mL), and sodium cyanoborohydride (1 M in THF, 0.022 mL) and acetic acid (0.013 mL) were added. The mixture was stirred overnight. The solvent was evaporated under vacuum, and the residue was dissolved in EtOAc (5 mL) and washed with saturated aqueous solution of NaHCO 3 (2 x 2 mL) and brine (2 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 100 \ 0 to 97 \ 3) to give the title compound (0.070 g). m \ z ([MH] +) = 798.

EXAMPLE 124 (11 21?, ¾-3-Decladoinosyl-11,12-d-Desoxy-6-0-met8l-3-oxo-12,11-roxycarbonyl- (3- (5-methoxy-1H-pyrrolor-3,2-blpyridin -1-H) -propylamino) - methyleneol-erythromycin A A solution of intermediate 118 (0.065 g) in acetonitrile (2.5 mL), and an aqueous solution of 3M HCl (2.5 mL), were stirred at 60 ° C for 8 hours. The reaction mixture was allowed to reach room temperature, and then it was added dropwise to a solution of Example 7 (0.040 g) dissolved in anhydrous acetonitrile (1 mL), maintaining the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCC > 3. The mixture was stirred at room temperature for 24 hours. Acetic acid was added until it reached a pH of 5-6, followed by sodium cyanoborohydride (1M in THF, 0.060 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCC > 3 (3 mL), and the mixture was extracted with DCM (3x5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with DCMWleOH from 100 \ 0 to 95 \ 5), to give the title compound (0.014 g). 1 HR N (CDCl 3) d: 7.66 (d, 1 H), 7.25 (d, 1 H), 6.62 (m, 1 H), 6.51 (d, 1 H), 4.40 (m, 1 H), 4.30 (d. m, 1 H), 4.15 (m, 1 H), 4.00 (s, 3 H), 3.03 (m, 1 H), 3.05-2.88 (m, 2H), 2.30 (m, 1 H), 2.06 (m , 1 H), 1.96 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 125 (11. £ 21 ?,) -3-Decladoinosyl-11, 12-dideoxy-6-Q-metH-3-oxo-12,11-roxycarbonyl- (2-r3- (1,3-thiazole-2) -yl) -1 H-pyrazole-1-n-ethylamino) -methylene-1-erythromycin A A solution of intermediate 119 (0.015 g) in acetonitrile (1 ml_), and an aqueous solution of 3M HCl (1 ml_), were stirred at room temperature for 16 hours, and heated at 50 ° C for 8 hours. The reaction mixture was allowed to reach room temperature, and then it was added dropwise to a solution of Example 7 (0.033 g) dissolved in anhydrous acetonitrile (1 mL), maintaining the pH of the solution on a scale of 6-7 by the addition of saturated aqueous solution of NaHCO3. The solution was stirred at room temperature overnight. Acetic acid was added until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 in THF, 0.025 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCO 3 (3 mL) was added, and the mixture was extracted with DCM (3x5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in MeOH (1 mL) and stirred overnight. After evaporating the solvent, the crude material was purified by flash chromatography (eluting with DCMVMeOH from 100 \ 0 to 97 \ 3) and by preparative LC (A \ B from 80 \ 20 to 10 \ 90 in 20 minutes), to give the title compound (0.014 g). 1 H-NMR (CDCl 3) d: 7.80 (d, 1 H), 7.69 (d, 1 H), 7.27 (d, 1 H), 6.76 (d, 1 H), 5.63 (dd, 1 H), 4.33 (m, 3 H), 4.23 (m, 2H), 3.84 (m, 1 H), 3.57 (m, 1 H), 3.35 (m, 2H), 3.22 (m, 1 H), 3.10-3.00 (m , 2H), 2.64-2.50 (m, 2H), 2.50 (s, 3 H), 2.33 (s, 6 H), 2.30 (s, 1 H), 1.90 (m, 1 H), 1 .80 -1.66 (m, 3 H), 1 .60-1.40 (m + s, 1 H + 3 H), 1.40-1.20 (m, 4 * 3H + 1 H), 1.14 (d, 3 H), 1 .09 (d, 3 H), 0.86 (t, 3 H).

EXAMPLE 126 I11 £ 21R, 5) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (4-phenyl-1 H-imidazole-1 - il) -ethylamino) -methyleneol-erythromycin A A solution of intermediate 120 (0.023 g) in acetonitrile (0.5 mL), and an aqueous solution of 3M HCl (0.7 mL), were heated at 70 ° C for 24 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 7 (0.039 g) dissolved in anhydrous acetonitrile (0.5 mL), maintaining the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCC > 3. The solution was stirred at room temperature for 6 hours. Acetic acid was added until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.0.58 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the organic solvent, the aqueous phase was extracted with EtOAc (3x5 mL). The organic layer was washed with brine (3 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with DCMWleOH from 97 \ 3 to 95 \ 5) to give the title compound (0.026 g). 1 H-NMR (CDCl 3) d: 7.80 (d, 2 H), 7.58 (d, 1 H), 7.45 (d, 1 H), 7.36 (t, 2 H), 7.21 (m, 1 H), 4.21 (m , 1 H), 4.14-4.07 (m, 2H), 3.30-3.20 (m, 2H), 3.07 (m, 1 H), 2.29 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 127 (11, 21 /? 5) -3-Decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (4-thien-2- il-1H-imidazol-1-yl) -ethylamino) -methyl ene-erithromycin A A solution of intermediate 121 (0.088 g) in acetonitrile (1.5 mL) and an aqueous solution of 3M HCl (1 mL) was heated at 70 ° C for 24 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 7 (0.100 g) dissolved in anhydrous acetonitrile (1 mL), keeping the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCO 3. The solution was stirred at room temperature for 6 hours. Acetic acid was added until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.150 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the organic solvent, the aqueous phase was extracted with EtOAc (3x5 mL). The organic layer was washed with brine (3 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with DCM \ MeOH from 97 \ 3 to 95 \ 5). The obtained compound was dissolved in MeOH (5 mL), and stirred overnight at room temperature. After evaporating the solvent, the residue was purified by flash chromatography (eluting with DCM vIeOH from 100? 0 to 95? 5), to give the title compound (0.034 g). 1 H-NMR (CDCl 3) d: 7.54 (d, 1 H), 7.32 (d, 1 H), 7.28 (dd, 1 H), 7.15 (dd, 1 H), 7.01 (dd, 1 H), 4.20 (m , 1 H), 4.1 1-4.07 (m, 2H), 3.30-3.20 (m, 2H), 3.06 (m, 1 H), 2.30 (m, 1 H), 1.10 (d, 3 H).

EXAMPLE 128 (11 *, 21R,) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-Goxicarbonyl- (quininoin-2-methylamino) ) -methylene-erythromycin A A solution of Example 6 (0.050 g) and quinoline-2-carbaldehyde (0.015 g) in anhydrous toluene (3 mL) was heated at 10 ° C for 3 hours. The solution was allowed to reach room temperature and concentrated under reduced pressure. The residue was dissolved in MeOH (5 mL) and palladium palladium (10% by weight on carbon powder, 0.020 g) was added, and the mixture was stirred under a hydrogen atmosphere (1 atmosphere) for 1 hour. Filtration through a pad of celite eluting with MeOH (10 mL), and purification by flash chromatography (using DCM \ MeOH 90? 10), gave the title compound (0.009 g). H-NMR (CDCl 3) d: 8.74 (s, 1 H), 8.30 (d, 1 H), 8.21 (d, 1 H), 8.13 (td, 1 H), 7.83 (t, 1 H), 7.57 ( t, 1 H), 7.30 (t, 1 H), 5.16 (bs, 1 H), 3.12 (m, 1 H), 2.93 (bs, 1 H), 1.29 (d, 3 H).

EXAMPLE 129 (11 «y, 21 g5) -3-Declado-nosyl-11,12-dideoxy-6-0-methyl-3-oxo-12.11-foxycarbonyl- (quinolin-3-ylmethylamino) -methanol erythromycin A A solution of Example 6 (0.050 g) and quinoline-3-carbaldehyde (0.016 g) in anhydrous toluene (3 mL) was stirred at 100 ° C for 15 hours. After evaporation of the solvent under reduced pressure, the residue was dissolved in MeOH (1 mL), and sodium cyanoborohydride (1 M in THF, 0.060 mL) and acetic acid (0.004 mL) were added. The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCO 3 (3 mL) was added, and the mixture was extracted with DCM (3x5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using DCM \ MeOH 94 \ 6), to give the title compound (0.007 g).

H-NMR (CDCl 3) d: 8.94 (d, 1H), 8.23 (d, 1H), 8.09 (d, 1H), 7.82 (d, 1H), 7.67 (t, 1H), 7.53 (t, 1H), 4.29 (d, 1H), 4.28 (m, 2H), 4.18 (m, H), 3.07 (m, 1H), 2.48 (m, 1 H), 1.10 (d, 3 H).

EXEMPL0130 (11 £ 21 /?,5)-3-Decladinosil-11.12-didesoxi-6-0-methyl-3-oxo-12,11- roxycarboni- (N 3- (4-pyridin-3-yl-1H- imidazol-1-in-propylacetamido) - metHenol-erythromycin A To a solution of Example 66 (0.010 g) in anhydrous DCM (0.4 mL), DMAP (0.050 g) and acetyl chloride (0.030 mL) were added in portions over 4 days. Water (2 mL) was added, and the mixture was extracted with DCM (3x5 mL). The organic phase was dried over a2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with DCM \ MeOH from 97 \ 3 to 95 \ 5). The compound was dissolved in MeOH (1 mL) and stirred overnight. Evaporation of the solvent gave the title compound (0.002 g). 1 H-NMR (CDCl 3) d: 8.97 (s, 1 H), 8.48 (d, 1 H), 8.07 (d, 1 H), 7.62 (s, 1 H), 7.39 (s, 1 H), 7.31 (m, 1 H), 5.53 (bm, 1H), 4.35 (d, 1H), 4.29 (m, 1H), 4.15 (m, 1H), 4.01 (d, 1H), 3.83 (m, 1H), 3.72 (q, 1H), 3.65 (bs, 1H), 3.57-3.52 (m, 3 H), 3.21 (m, 1H), 3.10 (m, 1H), 2.73 (m, 1H), 2.65-2.50 (m, 2H + 3 H), 2.39 -2.22 (m, 2H + 6 H), 2.00 (s, 3 H), 1.99 (m, 1H), 1.70-1.50 (m, 4 H), 1.46 (s, 3 H), 1.40 (d, 3 H) ), 1.29-1.23 (m, 7H), 1.26 (s, 3 H), 1.10 (d, 3H + 3 H), 0.95 (t, 3) EXAMPLE 131 (11 £ 21 / ?,.S) 3 - Decladinos H-1, 12-dideoxy-6-Q-metH-3-oxo-2.11-foxycarbonyl- (benzylcarbamate) -methylene-1-erythrornicin A To a solution of Example 7 (0.070 g) in anhydrous DCM (2 mL) cooled to 0 ° C, TEA (0.090 mL), DMAP (catalytic amount) and benzyl chloroformate (0.070 g) were added under nitrogen atmosphere. The mixture was stirred at 0 ° C for 3 hours. After reaching room temperature, saturated aqueous solution of NaHCO3 (3 mL) was added, and the mixture was extracted with DCM (2x5 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCMWleOH from 100 \ 0 to 98 \ 2). The obtained compound was dissolved in MeOH (1 mL) and stirred at room temperature overnight. Evaporation of the solvent gave the title compound (0.002 g). H-NMR (CDCl 3) d: 7.40-7.20 (m, 5 H), 5.81 (d, 1 H), 5.16 (m, 1 H), 5.08 (m, 1 H), 4.80 (bm, 1 H), 3.07 (m, 1 H), 2.44 (m, 1 H), 1.18 (d, 3 H).

EXAMPLE 132 (11 £ 217 ?,) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-2,11-roxycarbonyl- (fquinolin-2-ylmetHen) -amino) -metüenol-erythromycin A A solution of Example 6 (0.050 g) and quinoline-2-carbaldehyde (0.015 g) in anhydrous toluene (3 mL) was heated at 110 ° C for 3 hours. The solution was allowed to reach room temperature, and concentrated under reduced pressure. The residue was dissolved in MeOH (5 mL) and stirred for 16 hours. Evaporation of the solvent gave the title compound (0.050 g). 1 H-NMR (CDCl 3) d: 8.99 (d, 1 H), 8.47 (d, 1 H), 8.09 (d, 1 H), 7.58 (s, 1 H), 7.41 (s, 1 H), 7.30 (m, 1 H), 6.73 (d, 1H), 4.88 (dd, 1 H), 4.67 (s, 1 H), 3.08 (m, 1 H), 2.41 (d, 1 H), 1.16 (d, 3 H).

EXAMPLE 133 (1 §21 / ?,) -3-Decladinosil-11.12-d-deoxoxyl-2-fluoro-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (quinoxalin-2- ilsulfanyl) -acetamido) -methylene-1-erythromycin A To a solution of (quinoxalin-2-ylsulfanyl) -acetic acid (0.056 g) in anhydrous DMF (4 mL) under a nitrogen atmosphere, HATU (0.097 g) and DIPEA (0.053 mL) were added. The reaction mixture was stirred at room temperature for 20 minutes, and then Example 11 (0.160 g) was added. The reaction mixture was stirred at room temperature for 6 hours, then diluted with DCM (10 mL) and washed with an aqueous solution of 5% NaHCO 3 (10 mL). The aqueous phase was extracted with DCM (3x10 mL), and the combined organic layers were washed with an aqueous solution of NaHCC > 3 to 5% (10 mL), dried over Na 2 SO 4 and evaporated under reduced pressure. The residue was dissolved in MeOH (5 mL) and stirred at room temperature overnight. After evaporating the solvent, the crude material was purified by flash chromatography (DCM leOH 95 \ 5), to give the title compound (0.126 g). m \ z ([MHf) = 847. 1 H-NMR (CDCl 3) d: 8.63 (s, 1 H), 8.20 (d, 1 H), 7.99 (m, 2 H), 7.72 (t, H), 7.65 (t, H), 5.47 (dd, H), 4.36 (d, 1 H), 3.98 (s, 1 H), 3.92 (d, 1 H), 3.51 (m, 1 H ), 3.16 (m, 1 H), 3.02 (m, 1 H), 2.88 (m, 1 H), 2.64 (s, 3 H), 2.58 (m, 1 H), 2.36 (m, 1 H), 2.34 (s, 6 h2), 2.10 (m, 1H), 2.03 (m, 1 H), 1.97 (m, 1 H), 1.73 (m, 4 H), 1.60-1.40 (m, 8H), 1.23 ( m, 4 H), 1.15-1.01 (m, 9H), 0.90 (t, 3 H).

EXAMPLE 134 (11"¾21?,) -3-Deity-nosyl-11.12-clideoxy-2-fluoro-6-methyl-3-oxo-12,11-hydroxycarbonyl- (4- (2-hydroxy) -dimethoxy-phenyl) -4-oxo-butyramido) -methylene-erythromycin A To a solution of 4- (2-hydroxy-4,5-dimethoxy-phenyl) -4-oxo-butyric acid (0.031 g) in anhydrous DMF (2 mL), HATU (0.047 g) was added under nitrogen atmosphere. and DIPEA (0.025 mL). After stirring for 30 minutes, Example 10 (0.070 g) was added, and the mixture was stirred overnight. An aqueous solution of 5% NaHCO 3 (3 mL) was added, and the mixture was extracted with DCM (2x3 mL). The organic phase was dried over Na 2 SO and evaporated under reduced pressure. The residue was dissolved in MeOH (3 mL) and stirred overnight. After evaporation of the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH40H from 100 \ 0 \ 0 to 85 \ 15 \ 0.2), to give the title compound (0.027 g) . 1 H NMR (CDCl 3) 5: 12.46 (s, 1 H), 7.15 (s, 1 H), 6.72 (d, 1 H), 6.44 (s, H), 4.44 (m, 1 H), 3.91 ( s, 3 H), 3.34 (s, 3 H), 3.34 (m, 2H), 3.04 (m, 1 H), 2.70-2.52 (m, 2H), 2.34 (m, 1 H), 1.80 (d, 3 H), 1.17 (d, 3 H).

EXAMPLE 135 f11 21 > ?,) -3-Declado-nosyl-11,12-dideoxy-2-fluoro-6-0-methyl-3-oxo-12,11-roxycarbonH- (4- (3,4-dimethoxy-phenyl) -4-oxo-butyramido) -methylene1- erythromycin A To a solution of 4- (3,4-dimethoxy-phenyl) -4-oxo-butyric acid (0.029 g) in anhydrous DMF (2 mL), HATU (0.047 g) and DIPEA (0.025 mL) were added under nitrogen atmosphere. ). After stirring for 30 minutes, Example 10 (0.070 g) was added, and the mixture was stirred overnight. An aqueous solution of 5% NaHCO 3 (3 mL) was added, and the mixture was extracted with DCM (2x3 mL). The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was dissolved in MeOH (3 mL) and stirred overnight. After evaporation of the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH40H from 100 \ 0 \ 0 to 85 \ 15 \ 0.2), to give the title compound (0.024 g) . 1 H-NMR (CDCl 3) d: 7.64 (d, 1 H), 7.53 (m, 1 H), 6.89 (d, 1 H), 6.77 (d, 1 H), 4.40 (t, 1 H), 3.96 (s, 3 H), 3.94 (s, 3 H), 3.35 (m, 2H), 3.04 (m, 1 H), 2.70-2.55 (m, 2H), 2.34 (m, 1 H), 1.81 (d) , 3 H), 1.17 (d, 3 H).

EXAMPLE 136 (11", 21 >?,) -3-Decladoinosyl-11, 12-d-Deoxy-2-fluoro-6-O-methyl-3-oxo-12.11-roxycarbonyl- (4- (4 -methoxy-3-nitro-phenyl) -4-oxo-butyramido) -methyleneol-erythromycin A To a solution of 4- (4-methoxy-3-nitro-phenyl) -4-oxo-butyric acid (0.031 g) in anhydrous DMF (2 mL), HATU (0.047 g) and DI PEA (0.025 mL) were added under nitrogen atmosphere. After stirring for 30 minutes, Example 10 (0.070 g) was added, and the mixture was stirred overnight. An aqueous solution of 5% NaHCO 3 (3 mL) was added, and the mixture was extracted with DCM (2x3 mL). The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was dissolved in MeOH (3 mL) and stirred overnight. After evaporation of the solvent, the crude material was purified by flash chromatography (eluting with: DCM \ MeOH \ NH40H from 100 \ 0 \ 0 to 85 \ 15 \ 0.2), to give the title compound (0.030 g) . H-NMR (CDCl 3) d: 8.49 (d, 1 H), 8.20 (dd, 1 H), 7.15 (d, 1 H), 6.66 (d, 1 H), 4.40 (t, 1 H), 4.04 ( s, 3 H), 3.31 (m, 2H), 2.99 (m, 1 H), 2.73 (m, 1 H), 2.61 (m, 1 H), 2.18 (m, 1H), 1.18 (d, 3 H) ).

EXAMPLE 137 (11 £ 21>., Si-3-Decladinosl-11, 12-dideoxy-2-fluoro-6-Q-methyl-3-oxo-12. 1-roxycarbonii-f2- (4- fpiridin-3-in-1 ^ imldazol-1-yl) ^ thylamino) -methylene1- erythromycin A A solution of intermediate 51 (0.070 g) in acetonitrile (2.5 ml_), and an aqueous solution of 3M HCI (2.5 ml), were heated at 80 ° C for 24 hours. The reaction mixture was allowed to reach room temperature, and then added dropwise to a solution of Example 10 (0.070 g) dissolved in anhydrous acetonitrile (2 mL), maintaining the pH of the solution on the scale of 6-8. 7 by the addition of saturated aqueous solution of NaHCC > 3. The mixture was stirred at room temperature overnight. Acetic acid was added until it reached a pH of 5-6, followed by sodium cyanoborohydride (1 M in THF, 0.150 mL). The reaction mixture was stirred overnight at room temperature. After evaporating the solvent, saturated aqueous solution of NaHCC > 3 (3 mL), and the mixture was extracted with DCM (2x5 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (eluting with DCM \ MeOH \ NH4OH from 100? 0? 0 to 80 \ 20 \ 0.2), to give the title compound (0.006 g). H-NMR (CDCl 3) d: 9.05 (d, 1 H), 8.44 (d, 1H), 8.13 (m, 1 H), 7.65 (d, 1 H), 7.57 (d, H), 7.27 (m, 2H), 4.20-4.10 (m, 2H), 4.07 (bs, 1 H), 3.40-3.25 (m, 2H), 2.87 (m, 1 H), 2.32 (m, 1 H), 1.81 (d, 3 H), 1.08 (d, 3 H).

EXAMPLE 138 (11"£ 21 / ?,) -3-Decladoinosyl-11,12-dideoxy-2-fluoro-6-Q-methyl-3-oxo-12,11 - [oxycarbonyl- (3- (4- ( pyridin-3"il) -imidazol-1-in-propylamino) -methyl-ene-erythromycin A A solution of Example 10 (0.070 g) and intermediate 52 (0.035 g) in anhydrous acetonitrile (3.5 mL) was stirred at room temperature for 6 hours. After evaporating the solvent, the residue was dissolved in anhydrous MeOH (3 mL), and sodium cyanoborohydride (1 M in THF, 0.051 mL) and acetic acid (0.008 mL) were added. The mixture was stirred overnight. The solvent was evaporated under vacuum, and the residue was dissolved in DCM (10 mL) and washed with saturated aqueous solution of NaHCO 3 (2x10 mL). The organic layer was dried over Na 2 SO 4, concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ eOH \ NH4OH from 100 \ 0 \ 0 to 80 \ 20 \ 0.2), to give the title compound (0.012 g). m \ z ([MH] +) = 830. 1 H-NMR (CDCl 3) d: 8.99 (d, 1 H), 8.46 (dd, 1 H), 8.11 (dd, 1 H), 7.63 (s, 1 H), 7.40 (s, 1 H), 7.30 (m, 1 H), 5.45 (dd, 1 H), 4.42 (d, 1 H), 4.18 (m, 1 H), 4.08 (m, 1 H), 4.04 (m, 1H), 3.55 (m, 1H), 3.18 (dd, 1 H), 3.1 1 (m, 1H), 3.00 (m, 1 H), 2.92 (m, 1 H), 2.95 (s, 3 H), 2.95 (m, 1 H), 2.58 (m, 1 H), 2.52 (m, 1 H), 2.30 (s, 6 H), 1.95 (m, 2H), 1.83 (d, 3 H), 1.57 (d, 3 H), 1.7 (m, 1 H), 1.68 (m, 1 H), 1.60 (m, 1 H), 1 .33 (s, 3 H), 1.26 (s, 3 H), 1.25 (m, 1 H),), 1.25 (d, 3 H), 1.16 (d, 3 H), 1.09 (d, 3 H), 0.92 (t, 3 H).

EXAMPLE 139 f 11 £ 21 / ?, 5) -3-Decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - ((2-methyl-6-nitrophenyl) -ureido ) -2-ethylamino) -methyleneol-erythromycin A To a solution of Example 13 (0.039 g) in anhydrous DCM (2 mL) cooled to -10 ° C, a solution of 6-methyl 2-nitroisocyanate (0.010 g) in anhydrous DCM (2 mL) was added, and the The mixture was stirred at -10 ° C for 2 hours. The reaction mixture was quenched with saturated aqueous NaHCO3 solution (2 mL), and the aqueous phase was extracted with DCM (2 mL). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ MeOH from 97 \ 3 to 95 \ 5), to give the title compound (0.010 g). 1H-MN (CDCl 3) d: 7.97 (bs, 1H), 7.78 (d, 1H), 7.44 (d, 1H), 7.15 (t, 1H), 6.23 (bs, 1H), 4.22 (s, 1H), 3.45 (m, 1H), 3.26-3.19 (m, 2H), 3.08 (m, 1H), 2.91 (m, 1H), 2.32 (s, 1H), 1.12 (d, 3 H).

EXAMPLE 0140 (11 £ 21> a-2'-0-Acetn-3-Decladoinosyl-11,12-dideoxy-6-Q-allyl-3-oxo-12,11-foxycarbonyl- (cyano) -methyleneT-erythromycin A To a solution of intermediate 38 (0.33 g) in DCM (30 mL), Dess-Martin periodinane (0.300 g) was added in portions within 3 hours. A solution of Na2S203 (5% in saturated aqueous solution of NaHCO3, 20 mL) was added, and the mixture was stirred for 1 hour. The aqueous phase was extracted with DCM (2x50 mL), and the organic phase was washed with water (2x30 mL), dried over Na2SO4 and evaporated under reduced pressure. Purification of the crude material by flash chromatography (eluting with: DCM \ MeOH \ NH39.6 \ 0.3 \ 0.09), gave the title compound (0.13 g). 1 H-NMR (CDCl 3) d: 5.69 (m, 1 H), 5.43 (dd, 1 H), 5.09 (m, 2 H), 4.75 (m, 1 H), 4.73 (s, 1 H), 4.47 (d, 1 H), 4.39 (d, 1H), 3.91 (q, 1H), 3.70 (m, 2H), 3.63 (m, 1H), 3.21 (m, 1H), 3.20 (s, 1H), 3.12 (m, 1H), 2.70 (m, 1H), 2.65 (m, 1H), 2.26 (s, 6 H), 2.04 (s, 3 H), 1.94 (m, 1H), 1.70 (m, 1H), 1.65 (m, 1H), 1.60 (s, 3 H), 1.55 (m, 1H), 1.36 (d, 3 H), 1.33 (s, 3 H), 1.26 (d, 6 H), 1.13 (d, 3 H), 1.06 (d , 3 H), 0.93 (t, 3 H).

EXAMPLE 141 (11"21 / fl-3-Decladinosyl- 1, 12-dideoxy-6-0-allyl-3-oxo-12.11-hydroxycarbonyl- (cyano) -methylene T-erythromycin A A solution of Example 140 (0.005 g) in MeOH (0.5 mL) was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.003 g). 1 H-NMR (CDCIs) d: 5.71 (m, 1H), 5.44 (dd, 1H), 5.08 (m, 2H), 4.72 (s, 1 H), 4.43 (d, 1 H), 4.40 (d, 1 H), 3.94 (q, H), 3.72 (m, 2H), 3.62 (m, 1 H), 3.20 (m, 4 H), 2.68 (m, 1 H), 2.52 (m, 1 H), 2.29 (s, 6 H), 1.94 (m, H), 1.81 (m, 1 H), 1.65 (m, 1 H), 1.60 (m, 1 H), 1.61 (s, 3 H), 1.42 (d, 3 H), 1.35 (s, 3 H), 1.34 (d, 3 H), 1.26 (d, 3 H), 1.12 (d, 3 H), 1 .08 (d, 3 H), 0.93 (t, 3 H).

EXAMPLE 142 (11, 21 / ?,.S) -2'-0-Acetyl-3-decladinos.i-11, 12-d-deoxy-6-Q-allyl-3-oxo-12,11-roxycarbon » 1- (benzhydrylidenoamino) -metholene-erythromycin A To a solution of intermediate 42 (0.528 g) and EDC (0.35 g) in anhydrous DCM (40 mL) cooled to 0 ° C, DMSO (0.4 mL) was added. After 10 minutes at 0 ° C, a solution of pyridinium trifluoroacetate (0.36 g) in DCM (2 mL) was slowly added. After 10 minutes, the ice bath was removed. Two other EDC additions (0.35 g each), DMSO (0.4 mL each time) and pyridinium trifluoroacetate (0.36 g each time) were carried out. The reaction mixture was quenched with water (50 mL) and extracted with DCM (3x50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give the title compound (0.520 g). TLC: DCM \ MeOH \ NH3 20 \ 2 \ 0.2 (Rf = 0.39).

EXAMPLE 143 (11 -S 21?) -2'-0-Acet8l-3-decladinosyl-11,12-dideoxy-6-0-aHI-3-oxo-12,11-foxycarbonyl- (amine) - methylene1-erythromycin A A solution of Example 142 (0.52 g) in acetonitrile (66 mL) and aqueous HCl solution at 1.2N (154 mL) was stirred at room temperature for 1 hour. After neutralizing the mixture with solid Na 2 CO 3, and evaporating the solvent under reduced pressure, the mixture was extracted with DCM (3x50 mL). The organic layer was dried over a2SO4 and concentrated under reduced pressure to give the title compound (0.47 g). 1 H-NMR (CDCl 3) d: 5.88 (dd, 1 H), 5.70 (m, 1 H), 5.13 (d, 1 H), 4.75 (m, 1 H), 4.57 (s, 1 H), 4.44 (d, 1 H), 4.38 (d, 1 H), 3.91 (q, 1 H), 3.75 (q, dd), 3.61 (m, 1 H), 3.50 (m, 1 H), 3.24 (m, 1 H), 3.08 (m, 1 H), 2.70 (m, 1 H), 2.64 (m, 1 H), 2.46 (bs, 1 H), 2.26 (s, 6 H), 2.18 (m, 6 H) ), 1.60-1.40 (m, 5 H), 1.40-1.20 (m, 13 H), 1.15 (d, 3 H), 1.08 (d, 3 H), 0.88 (t, 3 H).

EXAMPLE 144 (11 £ 21 g) -3-Decladoinosyl-11, 12-d-Deoxy-6-Q-allyl-3-oxo-12.11 · fox8carbonyl- (amino) -methylene-1-erithromycin A A solution of Example 143 (0.002 g) in MeOH (0.3 mL) was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.002 g). 1 H-NMR (CDCl 3) d: 5.82 (dd, 1 H), 5.73 (m, 1 H), 5.14 (d, 1 H), 5.02 (d, 1 H), 4.54 (s, 1 H), 4.40 (d, 1 H), 4.38 (d, 1 H), 3.93 (q, 1H), 3.76 (m, 1 H), 3.62 (m, 1 H), 3.52 (m, 1 H), 3.24 (m, 1 H), 3.21 (m, 1 H), 3.09 (m, 1 H), 2.66 (m, 1 H), 2.50 (m, 1 H), 2.47 (m, 1 H), 2.28 (s, 6 H) ), 1.95 (m, 1 H), 1.85 (m, 2H), 1.80-0.80 (several m, 27H). m \ z ([MH] +) = 653.

EXAMPLE 145 I11, 21 / E5) -3-Declanedosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (quinolin-2-ylsulfanyl) - ethylamino) -methylene1 ^ ritromycin A To a solution of quinolin-2-thiol (0.008 g) in anhydrous DF (0.500 mL), sodium hydride (1.2 mg) was added, and the mixture was stirred at room temperature for 15 minutes, and then intermediate 24 was added. (0.025 g) and the reaction mixture was stirred at 60 ° C for 5 hours. The reaction mixture was diluted with DCM (3 mL) and washed with saturated aqueous NaHCO3 solution (1 mL). The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM \ eOH 98 \ 2), to give a compound which was dissolved in MeOH (1 mL) and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.010 g). Analysis of LCWIS (mobile phase: A \ B from 90? 10 to 10 \ 90 in 10 minutes, 10 \ 90 for 2 minutes, mass scale 150-1300 amu): retention time: 8.7 minutes, m \ z ([ MH] +) = 815.

EXAMPLE 146 (11 £.? // ?, 5) -3-Petzadinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (benzothiazol-2-ylsulfanyl) ^ tilamno) -methyllene-erithromycin A To a solution of benzothiazole-2-thiol (0.009 g) in anhydrous DMF (0.500 mL) was added sodium hydride (1.2 mg), and the mixture was stirred at room temperature for 15 minutes, and then intermediate 24 was added ( 0.025 g), and the reaction mixture was stirred at 60 ° C for 5 hours. The reaction mixture was diluted with DCM (3 mL), and washed with saturated aqueous solution of NaHCO 3 (1 mL). The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by flash chromatography (eluting with: DCM vleOH 98 \ 2), to give a compound that was dissolved in MeOH (1 mL), and stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave the title compound (0.012 g). Analysis of LC \ MS (mobile phase: A \ B from 90Y10 to 10 \ 90 in 10 minutes, 10 \ 90 for 2 minutes, mass scale 150-1300 amu): retention time: 8.5 minutes, m \ z ([ MH] +) = 821.

EXAMPLE 147 3-Pyridin-3-yl-acrylamide of (11'R21 / P, 5¾-3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-2,11-roxycarbonyl- (amino) -metholene-erythromycin A To 3-pyridin-3-yl-acrylic acid (1.3 mg), a solution of HATU (0.003 g) in anhydrous DMF (0.050 mL) and DIPEA (0.002 mL) in anhydrous DMF (0.050 mL) was added. mL), followed by a solution of Example 6 (0.005 g) in anhydrous DMF (0.050 mL). The reaction mixture was stirred at room temperature for 18 hours, then diluted with DCM (0.350 mL), washed with an aqueous solution of 5% NaHC03 (0.300 mL), and then passed through a syringe of phase separation. The aqueous phase was extracted with DCM (0.250 mL), and the collected organic extracts were evaporated under vacuum. The crude material was dissolved in DCM (0.700 mL), loaded in SCX cartridges (250 mg, loading 0.28 mmol / g, previously washed with 4 mL of MeOH), washed with MeOH (3.5 mL), and then the product it was eluted with NH3 (solution at 0.25M in MeOH, 1 mL), followed by MeOH (0.7 mL). The collected fractions were left in the NH3 / MeOH solution overnight. After evaporating the solvent, the title compound (0.002 g) was obtained. LC / MS analysis (mobile phase: A / B from 90/10 to 10/90 in 10 minutes, 10/90 for 5 minutes, mass scale 150-1200 amu): retention time: 5 minutes, m \ z ([MH] +) = 758.

EXAMPLES 148-312 EXAMPLE 148 3-BenzoM, 31d -oxo-5-yl-acri) amide of (11 ^ l P ^ -S -diddinosyl-H. ^ - dideoxy-6-0-methyl-3-oxo-12,11 -roxycarbonyl- (amino) -methyl-ene-erythromycin A EXAMPLE 149 (4-Methyl-2-oxo-2i-chromen-7-yloxy) -acetamide of (11 ^ 21 /? 5) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3- oxo-12, -roxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 150 r (Furan-2-carbonyl) -amino-1-acetamido of (1 ^ 21? Y5) -3-declaidinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonii- ( amino) -metholene-erythromycin A EXAMPLE 151 - (Thiophen-2-ylsulfanyl) -propionamide of (115y21 /?) -3-decidnosyl-11,12-dideoxy-6-Q-methyl-3-oxo -12,11-f-oxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 152 (Benzori, 31-dioxol-5-ylamino) -phenyl-acetamide of (11 £ 21 / g5) -3"decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 153 l "f3- (2-Chloro-phenyl) -5-methyl-isoxazole-4-carbonin-amino> -acetamide of (11, 21 / ?,« S) -3-decladinosyl-11,12-dideoxy -6-0-methyl-3-oxo-12,11-foxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 154 2-Acetylamino-3- (6-methyl-1 > ^ indole-3-yl) -propionamide of (11.S21 g) -3-decladinosyl-11,12-d-desox! -6- Q-methyl-3-oxo-12,11-roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 155 2-Acetylamino-3-f5-methyl-1 ^ indole-3-yl) -propionamide of (11S '^ l / E.fl-S-declaidinosiMI ^ -dideoxy-eO-methyl-S-oxo- ^ .IHoxte ^ methyleneol-erythromycin A EXAMPLE 156 () -3- (2,3-Dimethoxy-pyrimidin-5-yl) -acr! Lamide of (11"R21 /? 5) -3-decladinosyl-11, 12-didesoxt-6-0-metii -3-oxo-12,11 - [oxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 157 r5- (2-Methoxy-phenon-4-phenyl-4-G1, 2,4-tetra-3-ylsulfanyl-acetamide of (11 * 21 7,) -3-dec »adinos! l-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 158 2- (4-Methyl-r, 2,3-diazazol-5-ylsulfanin-propionamide of (11 £ 21 /? 5) -3-declanedinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo -12,1-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 159 (7-Methyl-thienor-3,2-o-pyrimidiri-4-ylsulfanyl) -acetamide of (115.21 / ¾) -3-declaidinosyl-11 , 12-dideoxy-6-0-met! L-3-oxo-12,1 -foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 160 f5- (2-Chloro-phenyl) -pyrimidin-4-ylsulfan -acetamide of (11, 21 / ?, 5) -3-declaidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amlno) -methylene-erythromycin A EXAMPLE 161 (4-Methyl-5-quinolin-6-yl-4H-ri, 2,41-triazol-3-ylsulfanyl) -acetamide of (11, 21 y ?,) -3-decladinosyl-11,12-d-deoxy-6 -Q-methyl-3-oxo-12,11-roxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 162 r (5-Bromo-furan-2-carbonyl) -am! No1-acetamide of (11 «R21>?,) -3-decidine-11,12-d-deoxy-6-Q-methyl -3-oxo-12,11-foxycarbonyl- (amino) methylene] -erythromycin A EXAMPLE 163 r (Thiophene-2-carbonyl) -amino-1-acetamide of (11 ^ l P ^ -S -diddinosyl- 11,12-d! Deoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -metHeno1- erythromycin A EXAMPLE 164 (4-Hydroxy-2-methyl-pyridin-3-yloxy) -acetamide of (11 21> 3) -dididinosyl-1,2-dideoxy-6-Q-methyl-3-oxo -12,11 -foxicarbonyl-famino) - methylenol-erythromycin A EXAMPLE 165 -f 1 / indol-3-yl) -acrylamide of (11 £ 21?,? 1-3 -distidinosyl-1 .12-dideoxy-6-0-metH-3-oxo-12.11-foxycarbonyl- (amino ) -methylene1 ^ ritromycin A EXAMPLE 166 4-Oxo-4-thiophen-2-H-butyramide of (11 21> 3) -diddinosyl-11,12-diodeoxy-6-0-methyl-3-oxo-2,11-foxycarbonyl - (amino) -methylene1- erythromycin A EXAMPLE 167 4- (4,5-Dimethoxy-8-2-nitro-phenyl) -4-oxo-butyramide of (1 *, 21 /? 5) -3 decidinosyl-11,2-dideoxy-6-Q-methyl- 3-oxo-12, 1-hydroxycarbonyl- (amino) - methylenol-erythromycin A EXAMPLE 168 - (2-Methoxy-phenyl) -4-oxo-butyramide of (11 £ 21 P,> -3-decladinosyl-11, 12-d-deoxy-6-0-methyl-3-oxo-12, 1-hydroxycarbonyl- (amine) -methyleneT- erythromycin A EXAMPLE 169 4-Oxo-4-pyridin-3-yl-butyramide of (1: 21?,. S) -3-deciadinosH-11,12-dideoxy-6-Q-methyl-3-oxo-12, 11-Roxycarbonyl (amino) -methyleneol-erythromycin A EXAMPLE 170 - (4-Methylsulfanyl-phenyl) -4-oxo-butyramide of (11 «¾217g« S) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- famíno) -metíleno1- erythromycin A EXAMPLE 171 3- (1> yimidazole-4-iD-acrylamide of (11 21?, 5) -3-declanedinosl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11- f oxycarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 172 -Tien-2-yl-butyramide of (11 S21 /? S) -3-dec) adinosi. 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxcarbonyl-amino) -methylene-1-erythromycin A EXAMPLE 173 3- (1y-qndol-3-in-propionamide of (11 121 /? V3 -decladinosyl-11.12-dideoxy-6-Q-methyl-3-oxo-12.11-roxycarbonyl) - (amino) -methylene1- erythromycin A EXAMPLE 174 (Pyridin-4-ylsulfanyl) -acetamide of (11 21?, 5) -3-declanedinosH-11. 2- dideoxy-6-Q-methyl-3-oxo-2.11-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 175 (Pyrimidin-2-ylsulfanyl) -acetamide of (11 »?, 21> g) -3-decladinosyl-11,12-dideoxy-e-0-methyl-3-oxo-12,11-foxycarboni amino) -methylene1- erythromycin A EXAMPLE 176 f (Pyridine-3-carbonin-aminol-acetamide of (11?, S \ -3-dec \ ad \ nos \\ - 11, 12-dideoxy-6-0-methyl-3-oxo-12.11-hydroxy) Carbonyl- (amino) -methylene'I- erythromycin A EXAMPLE 177 (-3-Pyridin-4-yl-acrylamide of (11 .21? "Fl-3-declaidinosiM 1,12-dideoxy-6-Q-methyl-3-oxo-2, -roxycarbon) - (amino) -methylene] -erythromycin A EXAMPLE 178 (£) -3-Pyrid! n-4-yl-acrylamide from (11 «R21>?,« S) -3-declaidinosyl-11, 12-dideoxy- 6-Q-methyl-3-oxo-12,11-hydroxycarbonyl-famino) -methylene-1-erythromycin A EXAMPLE 179 r2-f6-Methyl-pyridin-2-yl) -1-phenyl-ethylsulfanin-acetamide of (1 J, 21 g) -3- decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo -12,11 -roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 180 [(4-Oxo-yy-chromen-2-carbonin-amino-1-acetamide of (11"£ 21> 5) -3-decladoinosH-11, 12-dideoxy-6-Q-methyl-3-oxo- 12, 1-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 181 3- (1,4-Dioxo-3,4-dihydroftalazin-2 (1 y¾-) -1-propionamide of (11 ^ 21>,) -3-declanedinosyl-11,12-dideoxy-6-0- methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 182 (4-Methyl-ri, 2,3-triazole-5-sulfosyl) -acetamide of (11; 21?,) -3-declanedinosH-11,12-dideoxy-6-0-methyl-3- oxo-12,11-roxycarbonyl- (amino) methyleneol-erythromycin A EXAMPLE 183 (Benzothiazol-2-ylsulfanyl) -acetamide of (11 ^ 1 / ^ IS-declaidinosyl-H, ^ - d! deoxy-6-0 -methyl-3-oxo-12,11-roxycarbonyl- (amino) -methyl-ene-erythromycin A EXAMPLE 184 3- (1 ^ -Imidazole-n-proponamide of (11, 21 9,) -3-decidnosylM1,12-d, deoxy-6-0-methyl-3-oxo-12,11 -roxycarbonyl- (amino) -methylene] - erythromycin A EXAMPLE 185 -Pyridin-3-yl-propionamide of (11 ^ 21 g) -3-decladynosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-aroxycarbonyl- (amino) -methyleneol- Erythromycin A EXAMPLE 186 r (4-Methoxy-quinoline-2-carbonyl) -aminol-acetamide of (11> 21 / g5) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo- 12,11 -roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 187 (3-Phenyl-RI, 2,41-oxadiazol-5-ylamino) -acetamide of (11 «¾21>?,. S) -3-decladinosyl-11,12-d-deoxy-6-Q-methyl- 3-oxo-12.1 -foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 188 r4- (6-Oxo-1,4,5,6-tetrahydro-pyridazin-3-yl) -phenoxy-acetamide of (11) £ 21?, 5) -3-methsidiol-1, 12-dl-deoxy-6-Q-methyl-3-oxo-2, 1-oxocarbonyl- (amino) -methylene-1-erithromycin A EXAMPLE 189 3- (5-MetiM indol-3-yl) -propionamide of (11 £ 21>?,. S) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12 , 11 -foxicarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 190 4- (2,3-dioxo-2,3-dhydro-1) -dol-5-ll) -butyramide of (1 £ 21?) -3-declaidinosyl-11, 12-dideox8- 6-0-metlI-3-oxo-12,11 Hoxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 191 3- (1,3,8-Trimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropteridin-6-yl) -propionamide of (11 £ 21 /?,. S) -3-declaidinosH -1 ^ -didesoxUe-O-methyl-S-oxo- ^. Ll-roxycarbonyl-famino ^ ethyleneol ^ ri ^^ A EXAMPLE 192 3- (4-Oxo ^ J-dihydro-3H-pyrrolo [2,3-d] pyrimidin-5-yl) -propionamide (11 £ 21 /?, ^ - 3-Decladinos! L-11, 12-dideoxy-6-Q-methyl-3-oxo-12,1-foxycarbonyl- (amino) -metSleno1-erythromycin A EXAMPLE 193 r4- (1,3-Dimethyl-6-oxo-2-thioxo-2,3,6,9-tetrahydro-1 ^ purin-8-in-phenoxy-acetamide of (11 ^ 21 g S) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amine) -methylene-1-erythromycin A EXAMPLE 194 2-Benzoylam8no-3- (1 ^ indole-3-yn-propionamide of (1> 2 H) -3-methionine-11,12-dideoxy-6-0-methyl- 3-oxo-12, 1-roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 195 -Fenyl-4- (pyridin-2-ylcarbamoyl) -butyramide of (11.¾21 /? 5) -3-Decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (am'ino) -methylene1- erythromycin A EXAMPLE 196 3-Benzori, 31-dioxol-5-yl-2-benzoylamino-acrylamide of (1,11,7) -3-declaidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-2,11- roxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 197 3- (3-Phenyl-ureido) -3-thiophen-3-yl-propionamide of (11 ^, 21 ^, ^ - 3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo -12,1-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 198 - (Furan-2-yl) -propionamide of (11 £ 21 ^ 5) -3-decidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- ( amino) -methylene-1-erythromycin A EXAMPLE 199 2-Hydroxy-3- (1-indol-3-yl) -propionamide of (1 ^ l ^^ - S-declaidinosyl-11, 12-dideoxy-6-Q-metll-3-oxo-12.1- foxycarbonyl- (am! no) -methylene1- erythromycin A EXAMPLE 200 3- (5-Phenyl-1-pyrrol-2-yl) -prop-onamide of (11 ^ P ^ -S -diddinosyl- 11,12-dideoxy-6-Q-metH-3-oxo-12 , 11-Neocarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 201 4-Oxo-4-thiophen-2-yl-butyramide of (11 ^ 21 / ?, «S) -3-dedadinosyl-11,12-dideoxy- 6-0-methyl-3-oxo-12,11-roxycarboni-farnino) -methyleneol-erythromycin A EXAMPLE 202 (4-Methyl-pyrimidin-2-Hsulfan-i) -acetamide of (11"-21 /?,. S) -3-declamismosyl-11, 12-d-deoxy-6-Q- methyl-3-oxo-12,11 -foxcarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 203 4-G2-? , 3-Dioxo-l, 3-dihydro-2 > Βisoisole-2-n-phenyl-butyramide of (H ^ I / P ^ -S -diddinosyl-H. ^ - dideoxy-eO-methyl-S-oxo-^. H -roxycarbonyl- (amino) -methylene1 -erythromycin A EXAMPLE 204 - (2-Methyl-1-oxo-1,2-dihydroisoquinolin-3-yn-butyramide of (11 £ 21 /?) -3-decidines-11,12-dideoxy-6- 0-methyl-3-oxo-12,11-foxcarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 205 3-r3-f4-Methoxyphenyl) -1, 2,4-oxadiazol-5-in-propionamide of (W SH / ZSi-Q-decladyinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo -12,11 -foxicarbonyl-famino) - methyleneol-erythromycin A EXAMPLE 206 (4t6-Dimethyl-pyrimidin-2-ylsulfanyl) -acetamide of (11 *, 21.7.5) -3-decidinosil-11,12-dideoxy-6-0-methyl-3-oxo-12,11- foxycarbonyl-famino) - methyleneol-erythromycin A EXAMPLE 207 3-f2-Oxo-1,3-benzoxazoin-3 (2y ^ -yl-propionamide of (11 *, 21 >?,? 3-decladinosyl-11,12-dideoxy-6-0-methyl-3-? oxo-12, 1-roxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 208 4- (1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1 / ^ purin-8-yl) -butyramide of (11 «S21 /?,. S) - 3-Decladinosyl-11. ^ - dideoxy-eO-methyl-S-oxo- ^ -roxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 209 2-Formylamino-2- (1yyindol-3-yl) -propionamide of (11"£ 21?, 5) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12, 11-hydroxycarbonyl-famino) - methyleneol-erythromycin A EXAMPLE 210 4-Methyl-2-r (2-methylsulfanyl-pyridine-3-carbonyl) -amino-1-pentanamide of (115 *, 21 /?) -3-declaadymos-11, 12-dideoxy-6-Q -methyl-3-oxo-12,11- [oxocarbonyl- (amino) -methylene1-erythromycin A EXAMPLE 211 (3,5,6-Trichloro-pyridin-2-yloxy) -acetamide of (11. £ 21 /? 5) -3-Decladinosyl-11, 12-dideoxy-6-0-metU-3-oxo - 2,11-hydroxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 212 (5-Phenyl-pyrimidin-2-ylsulfanyl) -acetamide of (11 ^ 21 ^) -3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbon » - (amino) -methylene1- erythromycin A EXAMPLE 213 3-f6-Bromo-benzon.31-dioxol-5-in-2-cyano-acrylamide of (11 S.7AR, ^ -3-decladinosyl-11,12-dideoxy-6-0-methyl-3- oxo-12,11 - [oxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 214 3-r3- (4-Nitrophenyl) -1,2,4-oxadiazol-5-и-propionamide of (11 *, 21>,) -3-declanedinosyl-11,12-dideoxy-6-0 -methyl-3-oxo-12,11-foxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 215 3- (1, 3-Benzothiazol-2-yl) -propionamide of (11, 21?, "S) -3-decidinosium-11,12-dideoxy-6-0-methyl-3-oxo- 12,11-foxycarbonyl- (arnin) -methyl-ene-erythromycin A EXAMPLE 216 3- (3-Pyridin-2-yl-1,2,4-oxadiazol-5-SI) -propionamide of (11"R21?,) -3-decladoinosyl-11,12-dideoxy- 6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino-methyleneol-erythromycin A) EXAMPLE 217 4- (3-Pyridin-4-yl-1,2,4-oxadiazo! -5-yl) -butyramide of (11 ^, 21 /?) -3-declanedinosyl-11,12-dideoxy -6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) methyleneol-erythromycin A EXAMPLE 218 4- (3-Pyridin-2-yl-1,2,4-oxadiazol-5-yl) -butyramide of (11 £ 21?, 5) -3-declaidinosyl-11 , 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 219 3-r3- (4-Chlorophenyl) -1,2,4-oxadiazol-5-in-propionamide of (11 *, 21>,) -3-declaned H-1, 12-dideoxy-6-Q -met.l-3-oxo-12,11-roxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 220 4-r3- (4-Chlorophene-1,2,4-oxadiazol-5-yn-butyramide of (11"£ 21 /? 5) -3-decladinosyl-11,12-dideoxy -6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 221 4- (1,3-Benzodioxol-5-iD-butyramide of (11 «S: 21>?,) -3-decladinosyl-11,12-d-deoxy-6-0-methyI-3-oxo -12, 1-Roxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 222 4 < r3- (5-Oxo-2,3-d-hydroxy-5H-n, 31-thiazol-3,2-alpyrimidin-6-yl) -1,2,4-oxadiazol-5-yn-butyramide of (115 > 21 / ?,) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12.11-hydroxycarbonyl- (amino) -methylene erithromycin A EXAMPLE 223 4-r3- (3-Nitrophenyl) -1, 2,4-oxadiazo [-5-in-butyramide of (11 £ 21?, 5) -3- decladinosyl-11,12-dideoxy-6-Q- methyl-3-oxo-12,11-roxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 224 3-Pyrimidin-2-α-propionamide of (11 ^ 1 P ^ -S-decladynosyl-H, ^ -dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (amino ) -metHeno1- erythromycin A EXAMPLE 225 4- (2,3-Dihydro-1,4-benzodioxin-6-n-butyramide of (11 £ 21 and?, 5) -3-declanedinosyl-11,12-dideoxy-6-0-methyl -3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 226 3-r3-Chloro-5- (trifluoromethyl) pyridin-2-in-propionamide of (11 S, 2 J?, S) -Z-decladynosyl-11, 12-d-deoxy-6-Q- methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 227 - (1 > yindol-3-yl) -butyramide of (11.S21 /., S) 3-decladinosyl-11.12-d-deoxy-6-Q-methyl-3-oxo-12,11 -roxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 228 (5-Trifluoromethyl-pyridin-2-ylsulfanyl-acetamide of (11 «¾21t%) -3 'decladinosyl-1,12-dideoxy-6-Q-methyl-3-oxo- 2.1 - roxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 229 (Quinolin-8-yloxy) -acetamide of (11 «S21 / ?, 5) -3-declanedinos-8,12-dideoxy-6-0-methyl-3-oxo-2,11-roxycarbonii- (amino) -methylene1- erythromycin A EXAMPLE 230 3- (Quinoxalin-2-ylsulfanyl) -propionamide of (11 ^ l P ^ -S -diddinosyl- 11,12-dideoxy-6-Q-methyl-3-oxo-12, 11- [oxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 231 (2-Pyridin-2-yl-6-trifluoromethyl-pyrimidin-butylsulfanyl) -acetamide of (11, 21 /, ,. S) - 3 -decladinosyl-11,12-dideoxy-6-0-methyl- 3 »oxo-12,11-foxycarbonyl- (amino) -methylene1-erythromycin A EXAMPLE 232 3- (3-Chloro-5-trifluoromethyl-pyridin-2-yl) -lamide of (115.21?,) -3-declaidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo -12,11-Roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 233 -Pyridin-2-yl-lamide of (115.21?> 5) -3-decladinosll-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- ( arnino) -methylenol-erythromycin A EXAMPLE 234 (2,2-Dimethyl-4-oxo-chroman-7-yloxy) -acetamide of (11, 21 >?, "S) -3-decladinosyl-11,12-dideoxy-6-0 methyl-3-oxo-12,11-Foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 235 rS-S-Oxo ^ .S-dihydro-SH-thiazolorS ^ - ^ piYimidin-e-in-ri.Z. ^ oxadiazol-S-ylmethylsulfanyl-acetamide of (115.21 / ?, 5) -3-decladinosyl-11, 12-dideoxy-6- 0-methyl-3-oxo-12,11-roxycarbonyl- (amino) -methylene -erythromycin A EXAMPLE 236 (5,6,7,8-Tetrahydro-quinazolin-4-Hsulfanyl) -acetamidate of (11 ^ .21> g «S> -3- declared.) L-11,12-dideoxy -6-0-metH-3-oxo-12,11-foxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 237 Benzori, 31-dioxol-5-yl-proponamide of (15.21 / ?, 5) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12111-roxycarbonyl- (amino ) -methylene1- erythromycin A EXAMPLE 238 r5- (5-Nitro-furan-2-yl) -n, 3.41-oxadiazol-2-ylsulfanin-acetamide of (11521 / ?, 5) -3-deciadinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 239 (Pyridin-2-ylsulfanin-acetamide of (11 *, 21 / ?, <3-S-3 -deneddinil-11,12-d »deoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - (amino) -methylene1- erythromycin A EXAMPLE 240 [(2-Phenoxy-pyridine-3-carbonyl) -amino-1-acetamide of (11 ^ 21?,) -3-declad! Nosll-11, 2-dideoxy-6-0-methyl-3-oxo -12,11 -roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 241-Benzof1,31-dioxol-5-yl-2-cyano-acrylamide of (11.g21 g) -3-decladinosyl-11,12-d! Deoxy-6-0-methyl-3-oxo-12,11- foxycarbonyl- (am! no) -methyl-ene-erythromycin A EXAMPLE 242 (Benzenesulfonyl-pyridin-2-yl-amino) -acetamide of (11 «S21A *, ^ - 3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 243 (3-Chloro-methyl-2-oxo-2 ^ chromen-7-yloxy) -acetamide of (11 g21 /?) -3-declaidinosyl-1,2-dideoxy-6-Q-methyl- 3-oxo-2,1 -foxicarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 244 (5-Bromo-4-hydroxy-2-methyl-pyridin-3-yloxy) -acetamide of (11 S, 2 † ft, SZ-decladinosyl-11, 12-dideoxy-6-0-methyl-3 -oxo-12,11-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 245 (4-Methyl-4H-n, 2,41-triazol-3-ylsulfanin-acetamide of (11 S2 \ S,) -Z-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo- 12,11 -oxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 246 (2,2,5-Trimethyl-4-oxo-chroman-7-yloxy) -acetamide of (11 ^, 21 ^) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo - 2,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 247 3- (1- / g - Butyl-3,5-d-methyl-1-pyrazol-4-yl) -acrylamide of (11 *, 21 /?) -3-decladinosyl-11,12- d-Deoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 248 (1 lndol-3-yl) -acetamide of (11,121>? - 3 -denedidinyl-1,12-dideoxy-6,0-methyl-3-oxo-12,11-roxycarbonyl- (amino ) -methylene1-erithromycin A EXAMPLE 249 Tien-3-yl-acetamide of (11 «S21 and?, 5) -3-decladinosyl-11,12-dideoxy-6-0-met! L-3-oxo-12,11 -foxcarbonyl - (amino) -methylene1-erythromycin A EXAMPLE 250 (2-Phenyl, 3-thiazole-4-yl) -acetamide of (11 ^ 1 P ^ -S -diddinosyl-H, ^ -dideoxy-6-0-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 251 (1 / y ^ ndol-3-yl) -oxo-acetamide of (11 £ 21 /?) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12, 1 -roxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 252 Tien-2-yl-acetamide of (11 ^ iyp ^ -S -diddinosyl-IL ^ -dideoxy-eO-met8l-3-oxo-12,11 -foxicarbonyl- (amino) -methylene1-erythromycin A EXAMPLE 253 lmidazol-4-yl-acetamide of (11 ^ 21> 3) -dididinosyl-1, 12-dideoxS-6-0-methyl-3-oxo-12111-roxycarbonyl- (amino) -methylene-erythromycin TO EXAMPLE 254 I, 3-Benzodoloxol-5-yl-acetamide of (11 ^ 21>,) -3-decladinosyl-11.12-dideoxy-6-0-methyl-3-oxo-12,1-hydroxycarbonH- (am! no) -methyleneol-erythromycin A EXAMPLE 255 (2-P -razin-2-yl-1,3-thiazol-4-yn-acetamide of (11, 21> 5) -3-declaidinosyl-II, 12-dideoxy-6-0 -methi-3-oxo-12,11 -Foxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 256 (5-Bromo-1 / indole-3-yl) -acetamide of (11 ^ 21?,) -3-declanedinosyl-11,12-dideoxy-6-Q-methyl-3-oxo- 12,11-Roxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 257-Benzothien-3-yl-acetamide of (11 £ 21 ^ "Sl-SHJecladinosiMI ^ -didesoxí- eO-metil-S-oxo - ^ l 1 -roxycarbonH- (amino) -metholene-1-erythromycin A EXAMPLE 258 Pyridin-2-yl-acetamide of (11 21 /?) -3-declaidinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11 -foxicarbonyl- (am! No) - methylene-1-erythromycin A EXAMPLE 259 (1-Methyl- / 6-indol-3-yl) -acetamidate of (1152y?) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - (amino) -methylene1- erythromycin A EXAMPLE 260 (5-Fluoro-1-indol-3-in-acetamide of (1 ^ 1 P ^ -S -diddinosyl-H, ^ -d-deoxy-6-0-methyl-3-oxo-12,11 -foxicarbonyl- (amine) -metholene-erythromycin A EXAMPLE 261 (5-Methoxy-1> -dol-3-yl) -acetamide of (11 ^ l P ^ -S -diddinosyl-H, ^ -dideoxy-6-0-methyl-3-oxo-12,11- foxcarbonrl- (amino) -methylene-erythromycin A EXAMPLE 262 (4-Oxo-3,4-dihldroftalazin-1-yl) -acetamide of (11 ^ 21?, 5) -3-declaidinosyl- 11,12- dideoxy-6-0-methyl-3-oxo-12,1-hydroxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 263 (5-Methyl-2,4-dioxo-3,4-dihydropyrimidin-1 (2 ^ -yl) -acetamide of (1 S21 F, Sí-3-decladinosil-11, 12-dideoxy-6-0- methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 264 (1, 5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1-pyrazyl) -acetamide of (1 £ 21 /? 5) -3-decladinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 265 (5-Methoxy-2-methyl-1yyindol-3-yl) -acetamide of (11 £ 21> 5) -3-declared-nosyl 11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 266 dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl-famlno) -methylene-1-erythromycin A EXAMPLE 267 (5-Methyl-2-phenyl-1,3-oxazol-1-yl) -acetamide of (115.21 /? 5) -3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-3 -oxo-12,11-hydroxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 268 (6-Hydroxy-pyridazin-3-yl) - (4-methoxy-phenyl) -acetamide of (11, 21 g5) -3-declanedinosyl-11, 12-dideoxy-6-0-methyl-3 -oxo-12,11 -foxicarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 269 (5-Methyl-1-phenyl-1 y¾-pyrazolyl-1-yl) -acetamide of (11, 21> 5) -3-declaidinosyl-11,12-dideoxy-6-0-rnetyl-3 -oxo-12,1-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 270 (5-Methyl-2-phenyl-1,3-tlazol-4-yl-acetamide of (11. £ 21 /.,. S) -3-decladinosyl " 11, 12-dideoxy-6-0-methyl-3-oxo-12, 1 -foxicarbonii- (amino) -methylene-erythromycin A EXAMPLE 271 Pyridin-3-yl-acetamide of (11 £ 21 /? 3-1 -decladinosyl-11.12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxcarbonyl- ( amino) -methylene-1-erythromycin A EXAMPLE 272 5-Hydroxy-1 and »ndol-3-yl) -acetamide of (11: 21 g) -3-declanedinosiM 1, 12-dideoxy-6-0-methyl-3-oxo-12,11 -roxycarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 273 1-Benzothien-4-yl-acetamide of (115 *, 21 P,. S) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbonyl- ( amino) -methylene-1-erythromycin A EXAMPLE 274 2-Furyl-acetamide of (11 121> 5) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene1- Erythromycin A EXAMPLE 275 (2-Dlmethyl-1-indol-5-yl) -acetamide of (11 £ 21>?, -3-declanedinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12 , 11-roxycarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 276 4-f1,3-Benzothiazol-2-yl) -butyramide of (1 ¿21 ^) -3-declanedinosH-11,12-d-deoxy-6-0-methyl-3-oxo-12,11- Roxycarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 277 3- (2-Methyl-1'-ddol-3-yl) -propronamide of (11> y, 21 g «S) -3-decladinosyl-11,12-dideoxy-6-0-methyl -3-oxo-12,11-roxycarbon! L- (amino) -methylene-erythromycin A EXAMPLE 278 4-r3- (5-Nitrothien-3-yl) -1,2,4-oxadiazol-5-yn-butyramide of (11 ^ 21?,) -3-decidinosil-11,12-dideoxy-6- Q-methyl-3-oxo-12,11-roxycarbonyl- (amino) methyleneol-erythromycin A EXAMPLE 279 3-f1-Methyl-1 > y-benzimidazol-2-yl) -propionamide of (11 *, 21?, «$) - 3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 280 3- (4,6-Dimethoxy-pyrimidin-2-yl) -propionamide of (11 ^ 21> g), -3-declanedinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12, 11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 281 (6,7-Dmethoxy-isoquinolin-4-yl) -acetamide of (11 ^ lg ^ -S -diddinosyl- 1, 12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- famíno) -methiine erythromycin A EXAMPLE 282 r3- (2-Chlorophenyl) -5-methyl-isoxazole-4-in-acetamidate of (11 «S 21 P, 5) -3-decladinosyl-11,12-dideoxy-6-0-methyl- 3-Oxo-12,11-Roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 283 r4- 4-Oxo-1,2,3-benzotriazin-3 (4 HHDphenin-acetamide of (115.21?, 5) -3- decladynosyl-11,12-dideoxy-6-Q-methyl-3 -oxo-12,11-rox.}. carbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 284 r2-f2,4-Difluorophenyl) -1,3-thiazole-4-in-acetamide of (11,121 R,) -3- decladinosyl-11,12-dideoxy-6-Q-methyl-3- oxo-12,11 -foxicarbonyl-amino) - methyleneol-erythromycin A EXAMPLE 285 r2- ( { R (5- ethyl-1,3-thiadiazol-2-yl) thio1acetyl amino) -1,3-thiazole-4-in-acetamide of (11521?, ^ - 3-decladmosil-11.12- D-Desoxy-e-0-methyl-3-oxo-12,11-oxocarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 286 (2 r (Pyridin-2-lithium) acetynamino> -1,3-thiazole-4-in-acetamide of (11 S2?, S? -decladinosyl-, 12-dideoxy-6-Q -methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 287 (2- (r (Phenylthio) acetynamino) -1, 3-thiazol-4-yl) -acetamide of (11 S, 2 † / ?, Sl-Z-decladinosi-11, 12-dideoxy-6-Q -methyl-3-oxo-12,11-hydroxycarbonyl-famine) - methyleneol-erythromycin A EXAMPLE 288. { 2-r (4-Bromobenzoyl) aminoM, 3-thiazol-4-yl > acetamide of (11 .9,21,. S) -3-decladinosyl-1, 2-dideoxy-6-Q-methyl-3-oxo-12,1-dioxycarbonyl- (amino) -methylene] -erythromycin A EXAMPLE 289. { 2-r (3-Chlorobenzoyl) amino1-1, 3-thiazol-4-yl} -acetamide of (11 ^ 21 >?.) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12.11-roxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 290 Decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 291 n- (6-Chloropyridazin-3-yl) -1 ^ indole-3-in-acetamide of (11 i¾1> g-3-decidyl nosyl-1,12-dideoxy-6-Q-methyl-3 -oxo-12,11-roxycarbonii- (amino) - methyleneol-erythromycin A EXAMPLE 292 r2- (4-Chlorophenyl) -1,3-thiazole ^ 4-in-acetamide of (11.R2iy?,. S) -3-decidnosyl-11, 12-dideoxy-6-Q-methyl -3-oxo-12,11-hydroxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 293 f4- (4-Bromophenyl) -5-oxo-4,5-dihydro-1 ?? , 2,4-triazol-1-W-acetamide from (11: 21 /?, ^ - 3-decipadsl-11,12-dideoxy-6-0-methy1-3-oxo-12.11- foxcarbonyl- (amino) -methylene-erythromycin A EXAMPLE 294 (2-Oxo-l, 3-benzoxazol-3 (2½H1) -acetamide of (11 *, 21> 5) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3- oxo-12,11-foxycarbonyl- (amine) -methylene1- erythromycin A EXAMPLE 295 r2- (4-Methoxyphenyl) -1,3-thiazole-4-ill-acetamide of (11 «£ 21 / ?,« ¾-3-declaidinosl-11, 12-didesox¡-6-Q- methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 298 3-Furyl-acetamide of (11 21?, 5) -3-decladinosif-11,12-diodeoxy-6-0-methyl-3-oxo-12,1-roxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 297 (4-Metll-2-thioxo-1,3-thiazol-3 (2 ^ -yl) -acetamide of (11.R21 /?,. S) -3- decladinosyl-11,12-dideoxy-6- 0-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 298 r2- (Benzoylamino) -1,3-tiazol-4-in-acetamide of (11 *, 21 /?) -3-decidnosyl-11,12-dideoxy-6-0-methyl- 3-oxo-12,11-foxycarbonyl- (amlno) -methyleneol erythromycin A EXAMPLE 299 r4- (3,5-Dimethyl-1-pyrazol-1-H) -phenin-acetamide of m S, 21 /? S) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3 -oxo-2,11-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 300 G4- (1 Pyrazole-1-dipentane-acetamide of (11 £ 21 /? S) -3-declanedinosiM 1,12- dideoxy- 6-0-methyl-3-oxo-12,11-oxocarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 301 1-Benzofuran-4-yl-acetamide of (11 ', 21 /?) -3-decladinosii-11,12-dideoxy'i-6-0-methyl-3-oxo-12,11-foxycarbonyl- (amino) -methieno1- erythromycin A EXAMPLE 302 2-Acetylamino-3-f1 ^ indole-3-yl) -propionamide of (11 S21?, "Fl-3-declaidinosyl-11,12-dideoxy-6-Q-m-ethyl-3-oxo-12,11 - [oxycarbonyl- (amino) - methyleneol-erythromycin A EXAMPLE 303 3- (1,3-Benzodioxol-5-yl) -propionamide of (11 £ 21 5) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - (amino) -methyleneol-erythromycin A EXAMPLE 304 3- (1 > ^ Benzimidazol-2-yl) -propionamide of (11 ^ 21,) -3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene1- erythromycin A EXAMPLE 305 3- (6-Ethylsulfanyl-pyridin-3-yl) -acrylamide of (11 → 21 →., SV3-decladyinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11- Roxycarbonyl- (amino) -methylene'l-erythromycin A EXAMPLE 306 r4-Oxo-2- (1 > y-tetrazol-5-in-4 ^ chromen-7-yloxn-acetamide of (11 5 *, 21?,) -3-decladinosyl-11, 12-d Deoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methylene-erythromycin A EXAMPLE 307 3- (1-Oxoisoquinolin-2 (1-yl) -propionamide of (11 S ^ ftSl-Z-declanedinosi-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxcarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 308 2-Benzoylamino-3- (1 i ^ imidazol-4-yl) -propionamide of (11, 21> 7, «->) -3- decladinosil-11, 12-didesox! -6-Q- methyl-3-oxo-12,11-hydroxycarbonyl-famino) - methenol-erythromycin A EXAMPLE 309 3-Tien-2-yl-propionamide of (115.21?, 5) -3-decidnosyl-11,12-dideoxy-6,0-metii-3-oxo-12,11-foxycarbonii- ( amino) -methylene] -erythromycin A EXAMPLE 310 (3-Methyl-6-trifluoromethyl-3H-imidazor4,5-blpyridin-2-ylsulfanyl) -acetamide of (11, 21?, 5i-3-decidinosyl-11,12-dideoxy-6-Q-methyl- 3-oxo-12,11-roxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 311 r (2-It7-Tolisulfanyl-pyridine-3-carbonyl) -amino-acetamide of (11, 21?, S) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3- oxo-12,11 -Foxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 312 3-r3- (3-nitrophenol) -1,4, 2,4-oxadiazol-5-in-propionamide of (1, 5, 21 / ?, 5i-3-decidinosyl-11, 12-dideoxy- 6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (amino) -methyleneol-erythromycin A Examples 148-312 were obtained starting from example 6 (5 mg), following the same procedure reported for example 147. The name and amount of the starting material (ie, carboxylic acid) and the LC / MS analysis (retention time and m / z) of Examples 148-312, are reported in Table 1.

TABLE 1 TABLE 1 (CONTINUATION) 2- (4-Met.l- 7.3 158 [1, 2,3] thiadiazol-5-ylsulfanyl) - 1.8 813 8.0 propionic acid Acid (7- ethyl-thieno [3.2- 7.5 159 2.2 849 ¿pyrimidin-4-ylsulfanyl) -acetic 8.1 Acid [5- (2-chloro-phenyl) - 7.9 160 2.5 889 pyrimidin-4-ylsulfanyl] -acetic 8.4 Acid (4-Methyl-5-quinolin-6-yl-161 4 / [1, 2, 4] Iriazol-3-ylsulfanyl) - 2.6 6.3 909 acetic acid Acid [(5-Bromo-furan-2- 162 2.2 6.6 856 carbonyl) -amino] -acetic Acid [(Tiofen-2-carbonyl) - 163 1.6 6.3 794 amino] -acetic Acid (4-Hydroxy-2-methyl-164 1.6 5.2 792 pyridin-3-yloxy) -acetic acid 7. 3 165 3- (1 lndol-3-yl) -acrylic acid 1.7 796 8.1 4-Oxo-4-thiophen-2-iI- 6.0 166 1.7 793 butyric acid 6.6 4- (4,5-D-Methoxy-2-nitro- 6.3 167 2.5 892 phenyl) -4-oxo-butyric acid 6.8 4- (2-Methoxy-phenyl) -4-oxo- 68 1.9 6.3 817 butyric acid 4-Oxo-4-pyridin-3-yl- acid 5.0 69 1.6 788 butyric 5.4 TABLE 1 (CONTINUED) 4- (4-Methylsulfanyl-phenyl) - 170 2.0 6.6 833 4-oxo-butyric acid Acid 3- (1 / imidazol-4-yl) - 4.54 171 1.1 747 acrylic 4.87 6. 47 72 4-Thien-2-yl-butyric acid 1.4 779 7.17 Acid 3- (1/7-indol-3-yl) - 6.17 173 1.6 798 propionic 6.66 Acid (Pyridin-4-ylsulfanyl) - 5.02 174 1.4 Acetic 778 5.50 Acid (Pyrimidin-2-ylsulfanyl) - 175 1.4 5.59 779 acetic acid Acid [(Pyridine-3-carbonyl) - 176 1.5 4.51 789 amino] -acetic 5. 05 177 Acid (.}. -3-Pyridin-4-yl-acrylic 1.2 758 5.64 5. 02 78 Acid (£) -3-Pyridin-4-yl-acrylic 1.2 758 5.62 Acid [2- (6-Metii-pyridin-2-yl) -1 - 6.95 79 2.4 896 phenylethylsuiphanyl] -acetic 7.45 Acid [(4-0x0-4 H-chromen-2- 80 2.0 5.32 856 carbonyl) -amino] -acetic 3- (1, 4-Dioxo-3,4- 81 dihydroftalazin-2 (1 -il) - 1.9 4.54 843 propionic acid TABLE 1 (CONTINUED) Acid (4-Met.l- [1,2,3] thiazole (-5.88 182 1.6 799 5-ylsulfanyl) -acetic 6.39 Acid (Benxothiazole-2- 6.81 183 1.8.834 ilsulfanyl) -acetic 7.17 Acid 3- (1 / lmidazol-4-yl) - 4.39 84 1.2 749 propionic 4.59 4. 96 185 3-Pyridin-3-yl-propionic acid 1.2 760 5.42 Acid [(4-Methoxy-quinolin-2- 186 2.1 6.4 869 carbonii) -amino] -acetic Acid (3-Phenyl-187 [1, 2,4] oxadiazol-5-ylamino) - 1.8. 6.27 827 Acetic Acid [4- (6-Oxo-1, 4,5,6-188 tetrahydro-pyridazin-3 -il) - 2.0 5.32 857 phenoxy] -acetic Acid 3- (5-Methyl-1 indole-3-yl) - 6.51 189 1.7 812 propionic 7.00 Acid 4- (2,3-dioxo-2,3-dihydro-5.38 190 1.9 842 1 ^ indoI-5-yl) -butyric 5.80 Acid 3- (1, 3,8-Trimeti! -2,4,7- trioxo-1, 2,3,4,7,8- 4.60 191 2.4 903 hexahydropteridin-6-yl) - 4.92 propionic acid 3- (4-Oxo-4,7-dihydro-3 192 H-pyrrolo [2,3 -d] pyrimidin-5-yl) - 1.7 4.47 816 propionic Acid [4- (1,3-Dimethyl-6-oxo-2-6.53 193 thioxo-2,3,6,9-tetrahydro-1 - 2.8 955 6.88 purin-8-yl) -phenoxy] -acetic TABLE 1 (CONTINUED) 2-Benzoylamino-3- (1/194 2.5 6.5 917 ndol-3-yl) -propionic acid 3-Phenyl-4- (pyridin-2- 6.31 195 2.3 893 ilcarbamoyl) -butyric acid 6.62 Acid 3-Benzo [1, 3Jdioxol-5-il- 196 2.6 6.53 920 2-benzoylamino-acrylic Acid 3- (3-Phenyl-ureido) -3- 197 2.4 6.64 899 thiophen-3-yl-propionic acid 5. 91 198 3- (Furan-2-yl) -propionic acid 1.2 749 6.45 2-Hydroxy-3- (1-indol-3- 199 1.7-5.96 814) -propionic acid Acid 3- (5-FeniI-1 pyrrol-2-ii) - 7.13 00 1.8 824 propionic 7.48 4-Oxo-4-thiophen-2-yl- 5.86 01 1.5 793 butyric acid 6.42 Acid (4-Methyl-pyrimidin-2- 5.53 02 1.5 793 ilsulfanil) -acetic 5.85 Acid 4- [2- (, 3-Dioxo-1, 3-6.64 03 dihydro-2 isoindol-2-ii) -pheni]] - 2.6 918 7.16 butyric 4- (2-Methyl-1-oxo-1, 2- 04 2.0 5.76 854 dihydroisoquinol-3-yl) -butyric acid 3- [3- (4-Methoxyphenyl) - 6.51 05 1, 2,4-oxadiazol-5-yl] - 2.0 857 7.10 propionic acid TABLE 1 (CONTINUED) Acid (4,6-Dimethyl-pyrimidin-2- 5.74 206 1.6 807 ilsulfanyl) -acetic 6.10 Acid 3- (2-Oxo-1, 3- 5.95 207 benzoxazole-3 (2 7i) -l) - 1.7 816 6.36 propionic acid 4- (1,3-D! M9ti! -2,6-dioxo- 4.60 208 2,3,6,7-tetrahydro-1 // purin-8- 2.2 875 4.92 il) -butyric 2-Formylamino-2- (1 209 1.9 5.6 841 indole-3-yl) -propionic acid 4-Methyl-2 - [(2-6.60-210 methylsulfanyl-pyridine-3- 2.3.889 6.92 carbonyl) -amino] -pentanoic acid Acid (3,5,6-Trichloro-pyridin-2- 7.41 21 1 2.1 864 iloxi) -acetic 7.81 Acid (5-phenyl-pyrimidin-2- 6.76 212 2.0 855 iisuIfanil) -acetic 7.07 3- (6-Bromo-7.19 213 benzo [1, 3] dioxol-5-yl) -2-cyano- 2.4 904 7.84 acrylic acid 3- [3- (4-Nitrophenyl) -1, 2,4- 6.75 214 2.2 872 oxadiazol-5-yl] -propionic acid 7.29 3- (1, 3-Benzothiazol-2-yl) - 6.09 15 1.7 816 propionic acid 6.56 3- (3-Pyridin-2-yl-1, 2,4- 16 1.80 6.27 828 oxadiazol-5-yl) -propionic acid 4- (3-Pyridin-4-yl-1, 2,4- 6.57 17 1.9 842 oxadiazol-5-yl) -butyric acid 7.23 TABLE 1 (CONTINUED) 4- (3-Pyridin-2-yl-1, 2,4- 6.45 218 1.9 842 oxadiazol-5-yl) -butyric acid 7.05 3- [3- (4-Chlorophenyl) -1,2,4- 8.55 219 2.1 861 oxadiazol-5-yl] -propionic acid 9.15 4- [3- (4-Chlorophenyl) -1, 2,4- 8.68 220 2.2 875 oxadiazol-5-yl] -butyric acid 9.34 4- (1, 3-Benzodioxol-5-yl) - 7.71 221 1.7 817 butyric acid 8.43 4- [3- (5-Oxo-2,3-dihydro-5 H- [1, 3] thiazolo acid [3, 2- 5.97 222 2.5 917 a] pyrimidin-6-yl) -, 2,4-6,5-oxadiazol-5-yl] -butyric acid 4- [3- (3-Nitrophenyl) -1, 2,4- 8.07 223 2.3 886 oxadiazol-5-yl] -butyric 8.73 3-Pyrimidin-2-α-224 1.3, 5, 5, 761 propionic acid 4- (2,3-Dihydro-1, 4- 7.59 25 1.8 831 benzodioxin-6-yl) -butyric acid 8.31 3- [3-Chloro-5- 8.13 26 (trifluoromethyl) pyridin-2-yl] - 2.1 862 8.78 propionic acid 7. 77 27 4- (1 / indol-3-yl) -butyric acid 1.7 812 8.43 Acid (5-Trifluoromethyl-pyridine-8.06 28 1.9 846 2-isulfanyl) -acetic 8.43 29 Acid (Cholinolin-8-yloxy) -acetic 2.0 6.93 812 TABLE 1 (CONTINUED) Acid 3- (Quinoxalin-2- 230 1.9 7.82 843 ilsulfani) -propionic Acid (2-Pyridin-2-yl-6-955 231 trifluoromethyl-pyrimidin-4- 2.6 924 8.25 ilsulfani!) - acetic acid 3- (3-Chloro-5-3,31-trifluoromethyl-pyridin-2-yl) - 2.1 860 9.27 acrylic 6. 27 233 3-Pyridin-2-yl-acrylic acid 1.2 758 7.05 Acid (2,2-Dimethyl-4-oxo- 7.48 234 2.1 859 chroman-7-yloxy) -acetic 7.90 Acid [3- (5-Oxo-2,3-dihydro-5-thiazolo [3,2-c? pyrimidin-6-yl) - 6.27 235 2.7 935 [, 2,4] oxadiazol-5-6-ylmethylsulfanyl] -acetic acid (5,6,7,8-Tetrahydro- 7.23 236 1.8 833 quinazolin-4-ylsulfanii) -acetic 7.71 Benzo [1, 3] dioxol-5-il-7.65 237 1.6 799 propionic acid 8.37 Acid [5- (5-Nitro-furan-2-yl) - 7.34 38 [1, 3,4] oxadiazol-2-ylsulfanyl] - 2.2 880 7.70 acetic acid Acid (Pyridin-2-ylsulfanyl) - 39 1.4 7.05 778 acetic Acid [(2-Phenoxy-pyridine-3- 40 2.2 7.11 881 carbonyl) -amino] -acetic Acid 3-Benzo [1, 3] dioxol-5-il- 41 1.8 7.82 2-cyano-acrylic 826 TABLE 1 (CONTINUED) Acid (Benzenesulfonyl-pyridine- 242 2.4 7.05 901 2-yl-amino) -acetic Acid (3-Chloro-4-methyl-2-oxo- 7.95 243 2.2 877 2 / chromen-7-yloxy) -acetic 8.36 Acid (5-Bromo-4-hydroxy-2- 244 2.2 5.67 870 methyl-pyridin-3-yloxy) -acetic acid Acid (4-Methyl-4 H- 5.37 245 [1, 2,4] triazol-3-ylsulfanyl) - 1.4 782 5.61 acetic acid Acid (2,2,5-Trimethyl-4-oxo-246 2.2 7.95 873 chroman-7-yloxy) -acetic Acid 3- (1- / ¾? --Butil-3,5-7.336 247 1.8 831 dimethyl-1 pyrazol-4-i!) - acrylic 8.20 248 Acid (1 / ^ lndoI-3-il) -acetic 1.4 7.17 784 5. 7 249 Tien-3-yl-acetic acid 1.2 751 6.4 Acid (2-Phenyl-1,3-thiazole-4-ii) - 6.8 250 1.8 828 acetic 7.2 Acid (1 // -! Ndol-3-l) -oxo- 251 1.6 6.5 798 acetic acid 6. 0 52 Tien-2-il-acéic acid 1.2 751 6.7 53 1 lmidazol-4-yl-acetic acid 1.3 4.3 735 TABLE 1 (CONTINUED) Acid 1,3-Benzodioxol-5-il- 254 1.5 5.9 789 acetic acid Acid (2-Pyrazin-2-iM, 3-thiazol-255 1.8 5.5 830 4-il) -acetic Acid (5-Bromo-1 / -indol-3-yl) - 6.5 256 acetic 2.1 862 7.0 257 1-Benzothien-3-yl-acetic acid 1.6 6.8 801 258 Pyridin-2-yl-acetic acid 1.4 5.1 746 Acid (1-Methyl-Hndol-3-yl) - 259 1.6 6.6 798 acetic acid Acid (5-FIuoro-1 indole-3-yl) - 6.1 260 1.6 802 acetic 6.5 Acid (5-Methoxy-1 // indole-3-α) - 261 1.7 5.8 814 acéíico Acid (4-Oxo-3,4- 62 1.7 5 813 dihydroftalazin-1-yl) -acetic Acid (5-Methyl-2,4-d-oxo-3,4- 63 dihydropyrimidin-1 (2? - \\) - 1.5 4.6 793 acetic Acid (1,5-Dimethyl-3-oxo-2- ^ phenyl) -2,3-dihydro-1 / pyrazole-4- 2.0 5.4 855 il) -acetic Acid (5-Methoxy-2-methyl-1/65 1.8 6 828 indole-3-ii) -acetic TABLE 1 (CONTINUED) Acid (2-Methyl-1-indol-3-yl) - 6.2 266 1.6 798 acetic 6.6 Acid (5-Methyl-2-phenyl-1, 3- 267 1.8 6.7 826 oxazole-4-ii) -acetic Acid (6-Hydroxy-pyridazin-3-yl) - 268 2.1 5.5 869 (4-methoxy-phenyl) -acetic Acid (5-Methyl-1-phenyl-1 / 6.0 269 1.8 825 pyrazol-4-yl) -acetic 6.3 Acid (5-Methyl-2-phenyl-1, 3- 270 1.9 thiazo! -4-yl) -acetic 7.1 842 271 Pyridin-3-yl-acetic acid 1.2 4.8 746 Acid (5-Hydroxy-1 / β-ndol-3-yl) - 272 1.6 5 800 acetic acid 273 1-Benzothien-4-yl-acetic acid 1.6 6.7 801 74 Acid 2-Furil-acetic 1.1 5.7 732 Acid (2,3-Dimethyl-1 / indole-5- 6.4 75 1 .7 il) -acetic 812 7.0 4- (1, 3-Benzothiazol-2-yl) - 6.4 76 1.8 butyric acid 830 7.0 Acid 3- (2-Methyl-1 indol-3-yl) - 6.5 77 1 .7 812 propionic 7.0 TABLE 1 (CONTINUED) 4- [3- (5-Nitrothien-3-yl) - 6.8 2.3 892 1, 2,4-oxadiazol-5-yl] -butyric acid 7.4 3- (1-methyl-1 / 1.7.7.8 813 benzimidazol-2-yl) -propionic acid Acid 3- (4,6- Dirnetoxipirirnidin-2-il) - 1.7 5.9 821 propionic Acid (6,7-Dimethoxy-2.0 5.4 856 isoquinolin-4-yl) -acetic acid Acid [3- (2-Chlorophenyl) -5-methyl-6.8 2.1 860 isoxazol-4-yl] -acetic 7.3 Acid [4- (4-Oxo-1, 2,3-6,4 benzotriazin-3 (4/7) -yl) phenyl] - 2.3 890 6.9 acetic acid Acid [2- (2,4-Difluorophenyl) - 2.1 7.2 864, 3-thiazol-4-yl] -acetic Acid [2- ( { [(5-Methyl-1, 3,4-thiadiazol-2-yl) thio] acetyl} amino) - 2.7 5.5 939 1, 3-thiazol-4-yl] -acetic acid Acid (2- {[[(Pyridin-2-ylthio) acetyl] amino} -1, 3-thiazole-4- 2.5 6.1 918 yl) -acetic acid (2- {[(Phenylthio) acetyl]] amino.} -1, 3- 2.5 6.6 917 thiazol-4-yl) -acetic acid. { 2 - [(4- Bromobenzoyl) amino] -1, 3- 2.8 6.9 949 thiazol-4-yl} -acetic acid. { 2 - [(3-Chlorobenzoyl) amino] -1, 3- 2.4 6.8 905 thiazol-4-yl} -acetic TABLE 1 (CONTINUED) Acid { 2 - [(2- 290 CIorobenzoyl) amino] -1, 3- 2.4 6.3 905 thiazol-4-yl} -acetic Acid [1- (6-Chloropyridazin-3- 291 2.4 6.9 896 il) -1 / -indol-3-yl] -acetic Acid [2- (4-Chlorophenyl) -1, 3-292 2.1 7.5-862 thiazol-4-yl] -acetic Acid [4- (4-Bromophenyl) -5-oxo-293 4,5-dihydro-1β, 2,4-triazol-1 - 2.4 6.3 906 il] -acetic Acid (2-Oxo-l, 3-benzoxazole- 6.1 294 1.7 802 3 (2 7) -yl) -acetic 6.4 Acid [2- (4-Methoxyphenyl) -1, 3- 295 2.0 6.8 858 thiazol-4-yl] -acetic acid 296 3-Furyl-acetic acid 1.0 5.6 735 Acid (4-Methyl-2-thioxo-1, 3- 297 1.6 5.8 798 thiazole-3 (2 / V) -yl) -acetic Acid [2- (Benzoylamino) -1, 3- 98 2.2 6.2 871 thiazol-4-yl] -acetic acid Acid [4- (3,5-Dimethyl-1 7¿ 6.2 99 1.9 839 pyrazol-1-yl) phenyl] -acetic 6.7 Acid [4- (1-Pyrazol-1-yl) phenyl] - 00 1.7 5.9 81 1 acetic acid Acid 1-Benzofuran-4-il- 01 1.4 6.5 785 acetic TABLE 1 (CONTINUED) Acid 2-Acetylamino-3- (1 / 5.63 302 2.0 855 indole-3-yl) -propionic 5.71 3- (1, 3-Benzodioxol-5-yl) - 6.28 303 1 .6 803 propionic 6.76 acid 3- (1 Benzimidazole-2- 304 1 .6 5.55 799 il) -propionic acid 3- (6-Ethylsulfanyl-pyridine- 6.55 305 1 .7 818 3-il) -acrylic acid 7.34 Acid [4-Oxo-2- (1 etrazol-5- 306 2.4 4.88 ¡l) -4 H -chromen-7-yloxy] -acetic 897 Acid 3- (1-OxoisoquinoIin- 6.72 307 1 .8 826 2 (1 7) -i!) - propionic 6.92 2-Benzoylamino-3- (1 308 2.1 5.07 868 imidazol-4-yl) -propionic acid 6. 30 309 3-Thien-2-yl-propionic acid 1 .3 765 6.89 Acid (3-Methyl-6-trifluoromethyl-310 3 H -imidazo [4,5-b] pyridin-2- 2.4 7.96 900 ilsulfanyl) -acetic Acid [(2- Tolisulfanyl-pindin-7.57 31 1 2.5 91 1 3-carbonyl) -amino] -acetic 7.84 312 3- [3- (3-nitrophenyl) -1,2,4-7.92 2.2-872 oxadiazol-5-yl] -propionic acid 8.53 EXAMPLE 313 (2 7/2-Amlno-3- (1 ^ indole-3 -il) -proponamide of (11 21?, 5) -3- decladinosiI-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methylene -erythromycin A To (2 i) -e, -toxycarbonylamino-3- (1 7-indol-3-yl) -propynic acid (0.0025 g), a solution of HATU (0.003 g) in anhydrous DMF (0.050 mL) and DIPEA ( 0.002 mL) in anhydrous DMF (0.050 mL), followed by a solution of Example 6 (0.005 g) in anhydrous DMF (0.050 mL). The reaction mixture was stirred at room temperature for 18 hours, then diluted with DCM (0.350 mL), washed with an aqueous solution of 5% NaHC03 (0.300 mL), and then passed through a syringe of phase separation. The aqueous phase was extracted with DCM (0.250 mL), and the collected organic extracts were evaporated under vacuum. The residue was dissolved in a solution of 10% TFA in anhydrous DCM (0.300 mL), and the mixture was stirred for 1.5 hours. The solution was diluted with EtOAc (0.400 mL), and then the solvents were evaporated under reduced pressure. The raw material was dissolved in DCM (0.700 mL), loaded in SCX cartridges (100 mg, loading 0.75 mmol / g, prewashed with 4 mL of MeOH), washed with MeOH (4 mL), and then the product it was eluted with NH3 (solution at 0.25M in MeOH, 1.5 mL), followed by MeOH (2 mL), and the solvents were evaporated under vacuum. The residue was dissolved in MeOH (1.7 mL), and stirred overnight at room temperature. After evaporating the solvent, the title compound (0.001 g) was obtained. LC / MS analysis (mobile phase: A / B from 90/10 to 10/90 in 10 minutes, 10/90 for 3 minutes, mass scale 150-1000 amu): retention time: 4.95 minutes, m \ z ([MH] +) = 813.

EXAMPLES 314-320 EXAMPLE 314 f2) -2-Amino-3- (1-methyl-1-yyimidazol-5-yl) -propionarnide of (11 *, 21?, 5) -3-decladoinosyl-11,12-d-deoxy-6 -Q-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 315 (2?) - 2-Ainino-3-f1.3-t-azole-4-in-propionamide of (11 £ 21?, 5) -3- decladinosyl-11,12-dideoxy-6-Q- methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 316 (25) -2-Amino-3- (1,3-tiazol-4-yl) -proponamide of (11 £ 21 ./? 5) -3- decladinosyl-11,12-dideoxy -6-Q-methyl-3-oxo-12, -roxycarbonyl-famino) -methylene-erythromycin A EXAMPLE 317 (2 3-2-Amino-3-f1 ^ imidazol-5-yl) -propionamide of f 1 ^ 21 g) -3- decladinosyl-11, 12-d-deoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbonyl- (amino) -methylene-erythromycin A EXAMPLE 318 (2 i) -2-Amino-3-pyridin-3-yl-propionamide of (11, 21 y ?,) -3-methsid-1, 12-dideoxy-6-Q-methan-3-oxo- 12,11-foxicarbonyl-famino) -rnetileno1- erythromycin A EXAMPLE 319 (2) -2-Amino-3- (1-methyl-1y ^ im! Dazol-4-yl) -propionamide of (115.21 P,) -3- decladinosyl-11,12-dideoxy-6- 0-methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 320 (25) -2-Amino-3-pyrridin-2-yl-propionamide of (115.21 ^ 5) -3-declaidinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12 , 11-foxycarbonyl-famino) -methylene1- erythromycin A Examples 314-320 were obtained starting from Example 6 (5 mg), following the same procedure reported for Example 313.

The name and amount of the starting material (ie, carboxylic acid) and the LC / MS analysis (retention time and m / z) of Examples 314-320, are reported in Table 2.

TABLE 2 EXAMPLE 321 f2) -2-Amino-3-pyridin-1-proponamide of (11 ^, 21>, ">) -3-declaidinos-11,12-didesoxy -6-0-methyl-3-oxo-12,11-roxycarbonH-fam! No) -methylene-1-erythromycin A To acid (2.5) -2-. { [(9-fiuoren-9-ylmethoxy) carbonyl] arriino} -3-pyridin-4-yl-propionic acid (0.0032 g), a solution of HATU (0.003 g) in anhydrous DMF (0.050 mL) and DIPEA (0.002 mL) in anhydrous DMF (0.050 mL) was added, followed by a solution from Example 6 (0.005 g) in anhydrous DMF (0.050 mL). The reaction mixture was stirred at room temperature for 18 hours, then diluted with DCM (0.350 mL), washed with an aqueous solution of 5% NaHC03 (0.300 mL), and then passed through a syringe of phase separation. The aqueous phase was extracted with DCM (0.250 mL), and the collected organic extracts were evaporated under vacuum. The residue was dissolved in anhydrous DMF (0.350 mL), and then piperazinomethyl polystyrene resin (0.030 g, loading of 1.39 mmol / g) was added, and the mixture was stirred for 2.5 days. The mixture was filtered, and the resin was rinsed with DCM (0.400 mL), DMF (0.400 mL) and DCM (0.200 mL), and the filtrates were evaporated under reduced pressure. The crude material was dissolved in DCM (0.700 mL), loaded in SCX cartridges (100 mg, loading 0.75 mmol / g, pre-washed with 4 mL of MeOH), washed with MeOH (4 mL), and then the product it was eluted with NH3 (solution at 0.25M in MeOH, 1.5 mL), followed by MeOH (2 mL), and the solvents were evaporated under vacuum. The residue was dissolved in MeOH (1.7 mL), and stirred overnight at room temperature. After evaporating the solvent, the title compound (0.001 g) was obtained. LC / MS analysis (mobile phase: AB from 90/10 to 10/90 in 10 minutes, 10/90 for 3 minutes, mass scale 150-1000 amu): retention time: 3.98 / 4.70 minutes, m \ z ([MH] +) = 775.

EXAMPLES 322-327 EXAMPLE 322 (2) -2-Amino-3-. { 1-f (benzyloxy) metin-1 / ^ imidazol-5-yl) -propionamide of (11 *, 21?.) -3-decidinosyl-11,2-dideoxy-6-Q-methyl-3-oxo- 12.11 - Roxycarbonyl- (amino) -methyleneol-erythromycin A EXAMPLE 323 (2) -2-Amino-3- (1-benzyl-1 > ^ irriidazole-4-in-propionamide of (11 ^, 21?, 5) -3-decladinosyl-11,12-dideoxy -6-0-methyl-3-oxo-12,11-roxycarbonyl- (arnino) - methyleneol-erythromycin A EXAMPLE 324 f25) -2-Amino-3- (1 ^ imidazole-4-in-propionamide of (115.21 ^,) -3- decladinosyl-11,12-diodeoxy-6-0-methyl-3- oxo-12,11-roxycarbonyl-famino) - methyleneol-erythromycin A EXAMPLE 325 (2"fl-2-Amino-3-. {1-r (benzyloxyflmetin-1 W of (11, 21?,) - 3-Decladinosl-11,12-dideoxy-6-0-met! [-3-oxo-12,11-hydroxycarbonyl- (amino) -methylene-1-erythromycin A EXAMPLE 326 (3.S) -3-Amino-4- (1 ^ -indol-3-yl) -butyramide of (11 5; 21?, 5) -3-declaidinosyl- 1, 12-dideoxy-6-0- methyl-3-oxo-12,11-hydroxycarbonyl- (amino) -methylene 1-erythromycin A EXAMPLE 327 (2 / fl-2-Amino-3-pyridin-4-yl-propionamide of (11 ^ l ^ ^ - S-decladynosyl-11,2-dideoxy-6-Q-methyl-3-oxo-12, 1 -foxicarbonyl- (amino) -methyllenol-erythromycin A Examples 322-327 were obtained starting from example 6 (5 mg), following the same procedure reported for example 321. The name and amount of the starting material (ie, carboxylic acid) and the LC / MS analysis ( retention time and m / z) of examples 322-327, are reported in table 3.

TABLE 3 EXAMPLE 328 (11, 21?,) -3-Deciadinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (benzoyl-ureido) -methylene] -erythromycin A To a solution of Example 6 (0.005 g) in anhydrous THF (0.100 mL), a solution of benzoyl isocyanate (2.2 mg) in anhydrous THF (0.300 mL) was added. The reaction mixture was heated at 60 ° C for 24 hours. After cooling to room temperature, PS-Trisamine resin (charge of 3.62 mmol / g, 0.030 g) was added, and reacted at 60 ° C for 24 hours. After cooling to room temperature, the mixture was filtered, and the resin was rinsed with THF (2x0.240 mL), DCM (2x0.240 mL) and THF (4x0.170 mL), and the filtrate was evaporated. The residue was dissolved in MeOH (1 mL), and reacted at room temperature overnight. After evaporating the solvent, the title compound (0.003 g) was obtained. LC / MS analysis (mobile phase: AI 90/10 to 10/90 in 10 minutes, 10/90 for 2 minutes, retention time: 6.08 / 6.51 minutes, m \ z ([MHf) = 774.

EXAMPLES 329-398 EXAMPLE 329 (11 21?, "S) -3-Decladylnosyl-11.12-d8deoxy-6-0-metH-3-oxo-12,11-roxycarbonyl-phenyl-ureido) -methylene-1-erythromycin A EXAMPLE 330 (11 S, 21 /?,. S) 3- Decladlnosyl-11, 12-dideox8-6-Q-methyl-3-oxo-12,11-foxycarbonyl - ((2,6-dichloropyridine) 4-yl) -ureido) -methyl ene1-erythromycin A EXAMPLE 331 (11 21 y?, S) -3-Decladinosyl-11, 12-dideox! -6-Q-methyl-3-oxo-12,11- Roxycarbonyl - ((3,5-dimethylisoxazole ^ -SI) -ureido) -methyleneol-erythromycin A EXAMPLE 332 (£ 21 /? S) -3-Decladinosyl-11,2-dideoxy-6-Q-methyl-3-oxo-12,1-roxycarbonyl - ((pyridin-3-yl) -ureido) -methylene -erythromycin A EXAMPLE 333 fli ^ I / y ^ -S-Decladinosyl-ll .-- dideso ieO-methyl ^ -oxo-^. Ll-roxycarbonH-ff2,2; 4,4-tetrafluoro-4H-1,3-benzodioxin-6 -il) -ureido) - methyleneol-erythromycin A EXAMPLE 334 f11 £ 2iy? F5) -3-Decladylnosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonn - ((4- (A and ^ dimethylamino) pheny) - ureido) -methylenol ^ rrtromycin A EXAMPLE 335 (H ^ I P ^ -S-Decladinosyl-H. ^ - dideoxy-e-O-methyl-S-oxo-^. H -roxycarbonyl - ((4-nitrophenyl) -ureido) -methyl-iso-1-erythromycin A EXAMPLE 336 (II) R ^ -S-Decladinosyl-11. ^ - dideoxy-eO-methy1-S-oxo-1-l, -roxycarbonyl (3-nitrophenyl) -ureido) -methyl-1-erythromycin TO EXAMPLE 337 (11: 21?,) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl-f (2-nitrophenH) -ureido) -methylene-erythromycin A EXAMPLE 338 (11, 21 > 7, .S) -3-DecladinosM-11,12-dideoxy-6-Q-met8 > -3-oxo-12,11-roxycarbonyl - ((3,5-dinitrophenyl) -ureido) -methylene-1-erythromycin A EXAMPLE 339 (11 £ 21 >?,) -3-Decladinosil-11, 12-d-Deoxy-6-Q-metH-3-oxo-12,1-hydroxycarbonyl-f (4-methyl-2-nitrophenyl) -ure! do) -methienol-erythromycin A EXAMPLE 340 (11: 21y?, ^ - 3-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - ((2-methyl-4-n-trophenyl)) -ureido) -methylene1-erythromycin A EXAMPLE 341 Roxycarbonyl - ((2-methy1-5-nitrophenyl) -ureido) -methylene] -erythromycin A EXAMPLE 342 (11 £ 21?) -3-Decladoinosis-11,12-dideoxy-6-Q-methyl I-3-OXO-12,11-Roxycarbonyl - ((4-methyl-3-nitrophenyl) -ureido) -methylene-1-erythromycin A EXAMPLE 343 (11, 21 /? F) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbonyl- ((2-metH-3-nitrophenyl) -ure Do) -methylene1-erythromycin A EXAMPLE 344 (1 2 y?, ^ - 3-Declad! Nosil-1, 12-dideoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbonyl - ((2-methyl-6-nitrophenyl) -ureido ) -metHeno1-erythromycin A EXAMPLE 345 (1 S21 / ?, «S) -3-DecladinosiM 1,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl - ((5-chloro-2-nitrophenyl) -ureido) -methylene1-erythromycin A EXAMPLE 346 (II ^ I ^ P ^ -S-Decladinosyl-H. ^ - dideoxy-SO-methyl-S-oxo- ^. H -roxylcarbonyl-ff2-chloro-4-nitrophenol) -ureido) - methylene] -erythromycin A EXAMPLE 347 (H ^ IP ^ -S-Decladinosyl-H. ^ - dideoxy-SO-metii-S-oxo- ^ I -roxycarbonyl - ((4-chloro-3-nitrophenyl) -ureido) -methylene-1-erythromycin A EXAMPLE 348 (II ^ ZI g ^ -a-Decladinosyl-IL ^ -didesoxy-eO-methyl-S-oxo-IZH-foxycarbonyl - ((4-chloro-2-nitrophenyl) -ureldo) -met-leno1-erythromycin A EXAMPLE 349 (H ^ IÁ '^ - S-Decladinosi I. ^ - dSdeoxy-eO-methyl-S-oxo-ia.ll-roxycarbonyl - ((4-fluoro-3-nitropheni) -uretinate) -met leno1-erythromycin A EXAMPLE 350 (11 21 7 ^ -3-Decladinosl-11, 12-d-deoxy-6-Q-methyl-3-oxo-12.11 -rox »carbonii - ((2-fluoro-5-nitrophenin-ureido) -methylenol-erythromycin A EXAMPLE 351 fH ^ I P ^ -S-Decladinosyl-11 ^ -dideoxy-S-O-methyl-a-oxo- ^. H -roxycarbonyl-f (2-methoxy-5-nitrophenyl) -ureido) -methylene-lolithromycin A EXAMPLE 352 i 11 «R21 g5) -3-Declado-nosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.1-hydroxycarbonyl- ((2-methoxy-nitrophenii) -ureido) - methylene1-erythromycin A EXAMPLE 353 f11 £ 21 ^) -3-Decladinosyl-11,12-d-deoxy-6-Q-methyl-3-oxo-12.11-roxycarbonyl - ((4-methoxy-2-nitrophenyl) -ureido) -methylene -erythromycin A EXAMPLE 354 (11: 21 /?) -3-Decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-foxicarbonyl - ((4-methoxypheni) -ureido) -metileno1-erythromycin A EXAMPLE 355 (11. £ 21?) -3-Decladinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((3-methoxy-H) -urei'do ) -metíteno1-erythromycin A EXAMPLE 356 (11 £ 21?, 5) -3-Decladinosl-11, 12-diodeoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((2-methoxyphenyl "Ureido) -methyleneol- erythromycin A EXAMPLE 357 (11 £ 21 and?,) -3-Decladoinosyl-, 12-dideoxy-6-Q-methyl-3-oxo-2,1-hydroxycarbonyl - ((3,4-d-methoxyphenyl) - ureido) -methylene1-erythromycin A EXAMPLE 358 (1 21?,) -3-Decladinosyl-11,12-dideoxy-6-0-met.N3-oxo-12,11-foxycarbonyl ((2,4-dimethoxyphene-ureido) ) -methanol-erythromycin A EXAMPLE 359 (H ^ IP ^ -S-Decladinosyl-lt ^ -dideoxy-eO-methyl-S-oxo-I ^ H- [oxycarbonyl - ((2,5-dimethoxypheninureido) -methylene-erythromycin A EXAMPLE 360 ( 11 £ 21 / ?,.S)-3-Pecladinosil-11, 12-dideoxy-6-Q-metii-3-oxo-12,11-roxycarbonyl - ((3,5-dimethoxyphenyl) -ureido) -methylene erythromycin TO EXAMPLE 361 (1 S21?, S) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-Foxicarbonyl - ((2,6-dimethoxy-phenyl) -ureido) -methylene1-erythromycin A EXAMPLE 362 fH ^ I P ^^ - Decladinosyl-H. ^ - dideoxy-e-O-methyl-S-oxo- ^ I -roxycarbon M- (n, 3-benzodioxol-5-i'l) -ureido) -methieno1-erythromycin A EXAMPLE 363 fH ^ I P. ^ - S-Decladinosyl-H. ^ - dideoxy-eO-methyl-S-oxo - ^. H -roxycarbonyl - ((2-methoxy-5-methylphenol) -ureido) -methyleneol -erythromycin A EXAMPLE 364 (11 *, 21 >?, >) -3-Decladoinosil-11,12-d8-deoxy-6-O-methyl-3-oxo-12,11-Foxicarbonyl - ((2-etox Phenyl) -ureido) -methylene-1-erythromycin A EXAMPLE 365 (11, 21?,. S) -3-DecladinosiH 1, 12-dideoxy-6-Q-methyl-3-oxo-12, 1-roxycarbonyl - ((4-ethoxyphenyl) -ureido) -methyleneol-er Tromycin A EXAMPLE 366 (11, 21 /? 5) -3-Decladoinosi! -11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-oxocarbonyl- ((4 -phenoxyphenyl) -durate) -net} eno] -erithromycin A EXAMPLE 367 (11, 21 / ?, 5> -3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11 | roxycarbonyl - ((2-phenoxyphenyl) -ure8do) -tnet Leno1-erithromycin A EXAMPLE 368 (1, 21?,) -3-Pecladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonH-f (3-phenoxyphenyl) -ureido) -methylene-erythromycin A EXAMPLE 369 (l ^^ / gI- S- Decladinosyl-H.II- didesoxy-eO-methyl-S -oxo- ^. H -roxycarbonyl - ((3- (cyclopentyloxy) -4-methoxyphenyl) -ureido) -methylene1- erythromycin A EXAMPLE 370 (1, 21 >?,) -3-Pecladinosl-11, 12-d-deoxy-6-Q-met.N3-oxo-12,11-hydroxycarbonyl-f (5-chloro-2- rethoxyphenyl) -ureido) -methylene 1-erythromycin A EXAMPLE 371 (11 «£ 21>,) -3-Decladinosil-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((3-chloro-4-methoxyphenH) - urethane) -methylenol-erythromycin A EXAMPLE 372 (11. £ 21 /? 5) -3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (f5-loro-2,4-dimethoxyphenyl) - ureido) -methylene1-erythromycin A EXAMPLE 373 (11. £ 21 ?,.,. -3-Decladoinosyl-1, 12-dideoxy-6-Q-methyI-3-oxo-12,1-roxycarbonyl-f (4- (trifluoromethoxy) fe ^ A EXAMPLE 374 (11. £ 21 /., S) 3-Dec.adinosyl-11, 12-dideoxy-6-Q-met.l-3-oxo-12,1-foxcarbonyl-f (2- (trifluoromethoxy) phenyl) -ureido) -methieno1-erythromycin A EXAMPLE 375 (11 ', 21?, I-3-Decladoinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl-f (4- (difluoromethoxy) phenyl) -ureido) - methylene1-erythromycin A EXAMPLE 376 (11, 21?,) -3-Decladinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxcarbonyl-f (2- (difluoromethoxy) phenyl) -ureide ) -methylane] -erythromycin A EXAMPLE 377 (11521 / ?, 5) -3-Decladoinosyl-11, 12-d-Deoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- ( (4-yleythyl) fenin-ureido) -methylene-1-erithromycin A EXAMPLE 378 (11521?, I-3-Decanedinosl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbon! -1-phythylthio) phenyl) -ureido) - methylene1-erythromycin A EXAMPLE 379 (1521y ?,) -3-DedadmosfM1.12-dideoxy-6-0-methy »-3-oxo-12,11- [oxycarbonH - ((2- (methylthio) phenyl) -ureido)" methylene -erythromycin A EXAMPLE 380 (l ^ l P ^ -S-Decladinosyl-H. ^ - dideoxy-eO-methyl-S-oxo- ^. H -roxylcarbonyl- ((4-r (trifluoromethyl) thiophenyl) -ureido) -methylene -erythromycin A EXAMPLE 381 (11521 / 0.5.53) Decladinosyl-11, 12-dideoxy-6-Q-methyI-3-oxo-12.11-roxycarbonyl- ((4-acetylphenyl) -ureido) -methylene-1-erithromycin A EXAMPLE 382 (11521 R) -3-Declared! Nosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((3-acetylphenyl) -ureido) -methylene-erythromy A EXAMPLE 383 (11 «R21?, ^ - 3-Decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((4-cyanophenyl) -ureido) -methylene-1-erythromycin TO EXAMPLE 384 (11) 21?, 5) -3-Decladoinosyl-1, 12-dideoxy-6-0-methyl-3-oxo-2,1-FoxicarbonSl - ((3-cyanophenyl) -ureido) -methylene-erythromycin TO EXAMPLE 385 (1 £ 21 y ?,) -3-Declared as -11.12-dideoxy-6-Q-methyl-3-oxo-2.11 -foxicarbonyl - ((3- (trifluoromethyl) phenyl) -ureido) -methyl-1-erythromycin A EXAMPLE 386 (11 21?, "S) -3-Decladinosl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - ((4-chlorophenyl) -ureido) -methyleneol -erythromycin A EXAMPLE 387 (11 S21?, 5) -3-Decladoinosyl-11, 12-d-Deoxy-6-Q-methyl-3-oxo-12,11-roxcarbonyl - ((3-chlorophenol) -ureido ) -methylenol-erythromycin A EXAMPLE 388 (11 21 P, .S) -3-Deciad-nosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl - ((2-chlorophenyl) -ureido) -methylene-1-erythromycin A EXAMPLE 389 (11 S, 21 /? 5) -3-Decidinosil-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-foxcarbonyl - ((3, 4-d-chlorophenyl) -ureido) -metHeno1-erythromycin A EXAMPLE 390 (11 £ 21 >?, "S) -3-Pecladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl - ((4-fluorophenyl) -ureido) - methylene1-erythromycin A EXAMPLE 391 (1S, 2"\?,) -3-Decladinosil- 1, 12-dideoxy-6-0-metH-3-oxo-12, 1-foxycarbonyl - ((benzyl) -ureido) -methylene-1-erythromycin TO EXAMPLE 392 (11.S: 21 / ?,) -3-Decladoinosyl-11,12-d-deoxy-6-0-metH-3-oxo-12,11-foxycarbonyl - ((4-methoxybenzin-ureido) -methylene-1-erythromycin A EXAMPLE 393 (l ^ ^ yTT-S-Decladinosil-l l. ^ - dideoxy-e-O-methyl-S-oxo-^. H -roxycarbonyl - ((2-chlorobenzyl) -ureido) -methylene-erythromycin A EXAMPLE 394 (11 £ 21 and?, 5) -3-Decladinosl-11, 12-dideoxy-6-Q-metit-3-oxo-12,11-hydroxycarbon! - ((3,4-dichlorobenzyl) -ureido) -methylene-1-erythromycin A EXAMPLE 395 (11 £ 21 /? 5) -3-DecladinosiH 1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl - ((4-fluorobenzyl) ) -ureido) -methylene1-erythromycin A EXAMPLE 396 (11: 21 >?, 5¾-3-Decladoinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (f 4 -bromobenzyl) -uredo) -methylene1-erythromycin A EXAMPLE 397 (11: 21 yg ^ -3-Decladinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11- Foxicarbonyl - ((2-phenylethyl) -ureido) -methylene1-erythromycin TO EXAMPLE 398 (11: 21y ?,) -3-Decladinosl-11,12-d-deoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl - ((2-t-ene-2- ileyl) -ureido) -methylene-1-erythromycin A Examples 329-398 were obtained starting from example 6 (5 mg), following the same procedure reported for example 328. The name and amount of the starting material (ie, isocyanate) and the LC / MS analysis (time of retention and m / z) of examples 329-398, are reported in table 4.

TABLE 4 TABLE 4 (CONTINUATION) 1 - . 1 - . 1 - . 1 - . 1 - . 1 - . 1 - . 1-isocyanate-2-methyl-4-6.62 2.66 805 nitrobenzene 7.22 - 2-lisocyanate-1-methyl-4- 6.47 2.66 805 nitrobenzene 6.90 4-lisocyanate-1-methyl-2- 6.70 2.66 805 nitrobenzene 7.20 1-isocyanate-2-methyl-3-6.40 2.66 805 nitrobenzene 6.80 2-lisocyanate-1-methyl-3- 6.18 2.66 nitrobenzene 805 6.57 4-Chloro-2-isocyanate-1 - 7.11 2.97 825 nitrobenzene 7.83 2-Chloro-1-isocyanate-4- 6.86 2.97 825 nitrobenzene 7.57 1-Chloro-4-isocyanate-2- 6.91 2.97 825 nitrobenzene 7.51 4-Chloro-1-isocyanate-2- 7.05 2.97 825 nitrobenzene 7.84 1 -Fluoro-4-isocyanato-2- 6.48 2.72 809 nitrobenzene 7.00 1-Fluoro-2-isocyanate-4- 6.50 2.72 809 nitrobenzene 7.00 2-lisocyanate-1-methoxy-4- 6.40 2.90 821 nitrobenzene 7.00 TABLE 4 (CONTINUED) 1-Isocyanate-2-methoxy-4- 6.56 2.90 821 nitrobenzene 7.26 1-Isocyanate-4-methoxy-2- 6.48 2.90 821 nitrobenzene 7.13 5. 60 1 -socyanato-4-methoxybenzene 2.23 776 5.90 5. 70 1-lsocyanato-3-methoxybenzene 2.23 776 6.10 5. 40 1-isocyanate-2-methoxybenzene 2.23 776 6.10 4-lisocyanate-1, 2- 5.30 2.68 806 dimethoxybenzene 5.60 1-listonate-2,4- 5.60 2.68 806 dimethoxybenzene 6.10 2-lisocyanate-1, 4- 6.00 2.68 806 dimethoxybenzene 6.80 1-listonate-3,5- 6,17 2.68 806 dimethoxybenzene 6.64 2-lsocyanato-1, 3- 5.50 2.68 806 dimethoxybenzene 5.94 5. 60 5-lisocyanate-, 3-benzodioxol 2.44 790 5.90 2-lisocyanate-1-methoxy-4- 5.90 2.44 790 methylbenzene 6.60 BOX 4 (CONTINUED) 5. 80 364 1-Ethoxy-2-isocyanatobenzene 2.44 790 6.60 5. 80 365 1 - Ethoxy-4-isocyanatobenzene 2.44 790 6.10 7. 03 366 1 -socyanato-4-phenoxybenzene 3.16 838 7.30 6. 70 367 1-isocyanate-2-phenoxybenzene 3.16 838 7.30 7. 10 368 1-isocyanate-3-phenoxybenzene 3.16 838 7.40 2- (Cyclopentyloxy) -4-isocyanate- 6.60 369 3.49 860 1-methoxybenzene 6.80 4-chloro-2-isocyanate-1 - 6.89 370 2.74 810 methoxybenzene 7.63 2-Chloro-4-isocyanate-1- 6.10 371 2.74 810 methoxybenzene 6.40 1-Chloro-5-isocyanate-2,4- 6.10 72 3.19 810 dimethoxybenzene 6.50 1-lsocyanate-4- 7.13 73 3.04 830 (trifluoromethoxy) benzene 7.74 1-lisocyanate-2- 6.97 74 3.04 830 (trifluoromethoxy) benzene 7.63 1 - . 1 - . 1 - . 1 - (Difluoromethoxy) -4- 6.20 75 2.77 812 isocyanatobenzene 6.60 TABLE 4 (CONTINUED) 1 - (Difluoromethoxy) -2- 6.61 376 2.77 812 isocyanatobenzene 7.22 1-lisocyanate-4- 6.20 377 2.47 792 (methylthio) benzene 6.50 1-lisocyanate-3- 6.20 378 2.47 792 (methylthio) benzene 6.70 1-Isocyanato-2- 5.90 379 2.47 792 (methylthio) benzene 6.50 1-lsocyanate-4- 7.60 380 3.28 846 [(trifluoromethyl) thio] -benzene 8.20 5. 73 381 1 - (4-lsocyanatophenyl) ethanone 2.41 788 6.26 5. 83 382 1 - (3-lsocyanathophenyl) ethanone 2.41 788 6.34 6. 05 383 4-lsocyanatobenzonitril 2.15 771 6.59 6. 10 384 3-lisocyanabenzonitrüo 2.15 771 6.60 1-lisocyanate-3- 7.10 385 2.80 814 (trifluoromethyl) benzene 7.60 6. 70 386 1-Chloro-4-isocyanatobenzene 2.30 780 7.30 6. 69 387 1-Chloro-3-isocyanatobenzene 2.30 780 7.32 TABLE 4 (CONTINUED) 6. 69 388 1-Chloro-2-isocyanatobenzene 2.30 780 7.32 1, 2-Dichloro-4- 7.23 389 2.81 814 isocyanatobenzene 7.92 5. 80 390 1-Fluoro-4-isocyanatobenzene 2.05 764 6.20 6. 00 391 (Isocyanatomethyl) benzene 1.99 760 6.40 1 - (Isocyanatomethyl) -4- 5.92 392 2.44 790 methoxybenzene 6.28 1-CIoro-2- 6.38 393 2.51 794 (isocyanatomethyl) benzene 6.84 1,2-Dichloro-4-394 3.02 6.99 828 (isocyanatomethyl) benzene 1-Fluoro-4- 6.09 395 2.26 778 (isocyanatomethyl) benzene 6.40 1-Bromo-4- 6.70 396 3.17 838 (isocyanatomethyl) benzene 7.00 6. 30 397 (2-isocyanatoethylene) benzene 2.20 774 6.70 6. 10 98 2- (2-isocyanatoethyl) iiophene 2.29 780 6.50 EXAMPLE 399 (11, 21 y? "A-3-Decladinosil-1, 12-dideoxy-6-0-methyl-3-oxo-12,11 | Roxycarbonyl- (benzoyl-thioureido) -methylene-1-erythromycin A A solution of Example 6 (0.005 g) in MeOH (0.350 ml_) was reacted at room temperature. After evaporating the solvent, a solution of benzoyl isothiocyanate (2.4 mg) in DCE (0.400 mL) was added, and the reaction mixture was heated at 60 ° C for 26 hours. After cooling to room temperature, PS-Trisamine resin (charge of 3.62 mmol / g, 0.030 g) was added, and reacted at room temperature for 15 hours. The mixture was filtered and the resin was rinsed with DCE (2x0.230 mL) and DC (3x0.160 mL, 2x0.120 mL). AND! The filtrate was evaporated, to give the title compound (0.003 g). LC / MS analysis (mobile phase: A B from 90/10 to 10/90 in 16 minutes, 10/90 for 4 minutes, retention time: 9.1 / 10.0 minutes, m \ z ([MH] +) = 790.

EXAMPLES 400-425 EXAMPLE 400 (11 £ 21 and?, 5) -3-Decfadinosyl-11, 12-dideoxy-6-Q-methyp-3-oxo-12. 1-Roxycarbonyl - ((4 - (/ ¾A ^ dimetSlamino) -phenn-thioureido) -methylene-1-erythromycin A EXAMPLE 401 (11. £ 21?, 5) -3-Decladinosl-11, 12-dideoxy-6-0-methyl-3-oxo-12.11-hydroxycarbonyl- ((4- (V ^ / ^ diethylamino) phenyl) ) -thioureido) -methyleneT ^ ritrom »cina A EXAMPLE 402 (11 21 / ?,) -3-Declado-nosyl-11, 12-dideoxy-6-Q-methy1-3-oxo-2.11-foxycarbonyl - ((4- (A ^ dimethylamino) -1 - naphthyl) -thioureido) -metholene "| - erythromycin A EXAMPLE 403 (11 21?,) -3-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl - ((4-nitrophenyl) -thioureido) -methylene-1-erythromycin A EXAMPLE 404 (11 21 >?,) -3-Decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-oxocarboniN ((2-metiN 5 -nitrofenH) -thiouredo) - methylene] -erythromycin A EXAMPLE 405 (11 £ 21 y ?, -3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((2-chloro -4-n »trofenyl) -thioureido) -methyl-ene-erythromycin A EXAMPLE 406 (11 £ 21?, £ »-3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (f2-methoxy-4-nitrophenyl) -thioureido) - methylene-1-erithromycin A EXAMPLE 407 (1 £ 21>?, -3-Decladoinosyl, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl - ((4-methoxy-2-nitrophenyl) -thioureido) -metileno1 ^ ritrorri¡cina A EXAMPLE 408 (11 £ 21 and?, 5) -3-Decladoinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((2-methoxyphenyl) -thioureido) - methylene] -erythromycin A EXAMPLE 409 (11 £ 21 /?) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - ((2,5-dimethoxyphenyl) -thioureido) -nnethylene -triotin A EXAMPLE 410 (11 £ 21 y ?, -3-Decladinosil-11, 12-dideoxy-6-Q-metH-3-oxo-12,11-foxlcarbonyl - ((2-methoxy-5-methylphenyl) - thioure8do) -methylene-1-erythromycin A EXAMPLE 411 (11 → 21), -3-Decladoinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- ((4-methoxy-1,1'-bifen ^ A EXAMPLE 412 (1 £ 21 y?, 5l-3-Decladoinosii- 1, 12-d'deoxy-6-0-methyl-3-oxo-12.11-roxycarbonyl-f (4-ethoxyphenyl) -thioureido) -methylene1- Erithromycin A EXAMPLE 413 (H ^ g ^ - S-Decladinosyl-11. ^ - dideoxy-e-O-methyl-S-oxo-. H -foxycarbonyl - ((4- (benzyloxy) phenyl) -thioureido) -methylene-erythromycin A EXAMPLE 414 (H ^ IP ^ -S-Decladinosyl-H. ^ - dideoxy-SO-methyl-S-oxo-^. H -roxycarbonyl - ((5-chloro-2-methoxy-phenyl) -thioureido) -methylene1- Erromycin A EXAMPLE 415 (11> S: 21>,) -3-Decladoinosyl-11.12-dideoxy-6-0-methyl-3-oxo-12.1-roxycarbonyl - ((4- (methylthio) -phenyl) -thioureido ) -methylene] -erythromycin A EXAMPLE 416 (11S, 2 \, S) -3-Decladoinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12.11-hydroxycarbonH - ((benzyl) -thiouraido) -methyl-1-erythromycin EXAMPLE 417 (11, 21 > 7, .S) -3-PecladinosiM 1,12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl - ((2-furylmethyl) -thioureido ) -matiíeno1-erythromycin A EXAMPLE 418 (11 «S: 21 7,) -3-Decladinosyl-11,12-dideoxy-6-0-methan-3-oxo-12,11-roxycarbonyl-f (4-methoxybenzyl) -thiouredo) - methylene1-erythromycin A EXAMPLE 419 (11. £ 21/7,) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12.11-foxycarbonyl-f (2-methoxybenzyl) -thioureido) -metholene-1 erythromycin A EXAMPLE 420 (11. £ 21 and ?,) -3-Decladoinosyl-1, 12-dideoxy-6-0-met8l-3-oxo-12. 1 - roxlcarbonyl - ((2-chlorobenzyl) -thioureido) -methylene1-erythromycin A EXAMPLE 421 (H ^ I g.a-S-Decladinosyl-l ^^ -didesoxy-G-O-methyl-S-oxo-^. Ll-foxycarbonyl - ((3,4-dichlorobenzyl) -thioureido) -methylene-erythromycin A EXAMPLE 422 (11, 21 >?,) -3-Pecladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-2,11-hydroxycarbonyl - ((2-phenol-thioureido) -metHeno 1- Erythromycin A EXAMPLE 423 (11, 21?,) -3-DecladoinosiI-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl - ((2-morpholin--lethyl) -t Oureido) -methylenol-erythromycin A EXAMPLE 424 (11 £ 21,?) -3-Decladoinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl (2-f3,4-dimethoxyphenyl) ethynyl- thioureido) -methylene-1-er! thromicone A EXAMPLE 425 f 11 £ 21 y?,. S) -3-Decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxcarbonyl-f (2- (4-chlorophenol l) -ethyl) -thioureido) -methi [eno1-erythromycin A] Examples 400-425 were obtained starting from Example 6 (5 mg), following the same procedure reported for Example 399. The name and amount of the starting material (ie, socianate) and the LC / MS analysis ( retention time) of examples 400-425, are reported in table 5.

TABLE 5 TABLE 5 (CONTINUED) 3-lsothiocyanato-4-methoxy-1, 1'- 10.4 41 1 3.61 868 biphenyl 11.3 1-Etoxi-4- 9.2 412 2.68 806 Sothiocyanatobenzene 9.9 1 - . 1 - . 1 - (Benzyloxy) -4- 10.7 413 3.61 868 isothiocyanatobenzene 1 1.3 4-Chloro-2-isothiocyanato-1 - 9.4 414 2.98 826 methoxybenzene 10.5 1-lsothiocyanate-4- 9.4 415 2.71 808 (methylthio) benzene 10.2 416 (Isothiocyanatomethyl) benzene 2.23 9.5 776 417 2- (lsothiocyanatomethyl) furan 2.08 8.5 765 1- (lsothiocyanatomethyl) -4- 418 2.68 9.5 806 methoxybenzene 1 - (lsothiocyanatomethyl) -2- 419 2.68 9.6 806 methoxybenzene 1-Chloro-2- 420 2.75 10.2 810 (isothiocyanatomethyl) benzene 1, 2-Dichloro-4- 10.8 421 3.26 844 (isothiocyanatomethyl) benzene 1 1.1 422 (2-lso-thioanatoethyl) benzene 2.44 10.1 790 TABLE 5 (CONTINUED) EXAMPLE 426 3-Amino-isonicotinamide of (11 *, 21 ^) -3-declacínosH-11,12-dideoxí-6-0-methyl-3-oxo-12,11-roxicarbonil- (2- (amino) -ethylamino ) -methylene1- erythromycin A To 3-amino-isonicotinic acid (0.001 g), a solution of benzotriazol-1-yl-oxy-tris-pyrrolidin-phosphonium hexafluorophosphate (0.004 g) in anhydrous DMF (0.150 mL) and a solution of DIPEA (0.003 g) were added. mL) in anhydrous DMF (0.150 mL), followed by the addition of a solution of Example 13 (0.005 g) in anhydrous DMF (0.100 mL). The reaction mixture was stirred at room temperature for 48 hours, then diluted with DCM (0.600 mL), washed with an aqueous solution of NaHCC > 3 to 5% (0.500 mL), and then passed through a phase separation syringe. The aqueous phase was extracted with DCM (0.400 mL), and the collected organic extracts were evaporated under vacuum. The crude material was dissolved in DCM (0.500 mL), loaded onto an SCX cartridge (250 mg, loading 0.75 mmol / g), washed with MeOH (4 mL), and then the product was eluted with NH3 (solution a). 0.25M in MeOH, 1.5 mL). After evaporating the solvent, the title compound (0.003 g) was obtained. LC / MS analysis (mobile phase: A / B from 90/10 to 10/90 in 10 minutes, 10/90 for 2 minutes, mass scale 150-1300 amu): retention time: 4.99 minutes, m \ z ([MH] +) = 790.

EXAMPLES 427-601 EXAMPLE 427 5-Methyl-3-phenyl-isoxazole-4-carboxamide of (11 ^ 21y?) -3-decidnosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -etholamyl) -methyleneol-erythromycin A EXAMPLE 428 1, 5-DimetH-3-oxo-2-phenyl-2,3-dihydro-1-pyrazole-4-carboxamide of (11 «R21?, 5) -3-declanedinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) -methyleneT-erythromycin A EXAMPLE 429 2-Trifluoromethyl-n, 81-naphthyridine-3-carboxamide of (11.¾21 /?,. S) -3-decladinosyl-11, 12-dideoxy-6-Q-methyll-3-oxo-12,11 - [oxycarbonyl- (2- (amino) -ethylamino) -methylene1-erythromycin A EXAMPLE 430 -Nitro-2-oxo-2 / ¾-chromen-3-carboxamide of (11, 21 / P, 5) -3-declanedinosi-1 2-dideoxy-6-0-methyl-3-oxo-12, 11 oxycarbonyl- (2- (amine) -etiiarnine) - methyleneol-erythromycin A EXAMPLE 431 4-Amino-2-methylsulfanyl-pyrimidine-5-carboxamide of (11 S, 2?,? 3 -devindinosyl-1,12-dideoxy-6-Q-methyl-3-oxo- 12,11 -lOxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 432 -Cloro-1-methyl-1 ^ pyrazole-4-carboxamide of (11 ^ 21 g) -3-decladinosyl-1, 12-diodeoxy-6-Q-methyl-3-oxo-12,11- Roxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 433 -Pirazin-2-yl-thiazole-4-carboxamide of (H ^ I g ^ -S -diddinosyl-lly-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- ( amino) -ethylamino) - methylenol-erythromycin A EXAMPLE 434 3-Methyl-2-oxo-1,2-dihydro-quinoline-4-carboxamide of (11 ^ 21 ^,) -3- decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo- 12,11 -foxicarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 435 2-Methyl-imidazoH, 2, -. pyridine-3-carboxamide of (115 *, 21> 5) -3- decladinosyl-11,12-d-deoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (2) - (amino) -ethylamino) -methylene] -erythromycin A EXAMPLE 436 4-Methoxy-1,3-dimethyl-1 pyrazolor 3,4- > pyridine-5-carboxamide of (11. £ 21?,. S) -3-decladinosyl-11.12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (amine) -ethylamino) -methylene-erythromycin TO EXAMPLE 437 3-Methyl-5- (4-methyl-ri, 2,31-thiadiazol-5-ii) -isoxazole-4-carboxamide of (11 £ 21 /? 5) -3-decladoinosyl-11, 12- dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 438 4-Acetyl-1-methyl-1y-pyrrole-2-carboxamide of (11 21 /? S) -3-declanedosyl-11, 12-d-deoxy-6-Q-methyl-3- oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamine) - methylenol-erythromycin A EXAMPLE 439 6-M, 2.4lTriazol-1-yl-nicotinamide of (11 £ 21?, 5) -3-decladinosiI-1, 12-dideoxy-6-0-methyl-3-oxo-12,11-fox Carbonyl- (2- (amsno) -ethylamino) - metHenol-erythromycin A EXAMPLE 440 Isonicotinamide of (11 £ 21 → r ^) - 3-declaidinosyl-11,12-dl-desox! -6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) - methylene1-erythromycin A EXAMPLE 441 5-Oxo-2,3-dihydro-5H-thiazolof3,2-.? | Pyrimidine-6-carboxamide of (11 £ 21 /?) -3-decidnosyl-11, 12-d-deoxy- 6-Q-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino) -eti-lamino) -methylene] -erythromycin A EXAMPLE 442 5-Nitro-1 / pyrazole-3-carboxamide of (11 £ 21 >?,. S) -3-decladinosl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin TO EXAMPLE 443 2-Methylsulfanyl-nicotinamide of (11, 21 /? 5V3-declaidinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-2,11-roxycarbonyl- (2- (amine) - ethylamino) - methyleneol-erythromycin A EXAMPLE 444 -Hydroxy-2-oxo-2-chromen-3-carboxamide of (11 ^ l / g ^ -S -diddinosyl- 11,12-dideoxl · 6-0-metll-3-oxo-12,11-Goxicarboni ^ - (2- am ^ no) -etiamino) - methyleneol-erythromycin A EXAMPLE 445 Cinolin-4-carboxamide of (11 »¾21?,) -3-decidnosyl-11,12-dideoxy-6-0-methyl-3-oxo-2,11 -foxicarbonyl- (2- (amino)) -eti-lamino) -methylene1- erythromycin A EXAMPLE 446 -Amino-nicotinamide of (11 ^ 21?,) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene1- erythromycin A EXAMPLE 447 -Methyl-5-nitro-1 > and carboxy-4-carboxamide of (11 * f21 >?,) -3-dec [additives H-1,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- ( amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 448 J-Dimethylol-pyrazolor-5,1-gjri, 2,41-triazine-3-carboxamide of (11: 21 <?,) -3-decladinosyl-, 12-dideoxy-6-Q-methyl-3-oxo -12,11-foxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 449 -Metoxy-nicotinamide of (11 ¿: 21> 5) -3-declanedinosiM1,12-dideoxy-6-0 methyl-3-oxo-12,1 -foxicarbonii- (2- (amino)) -ethylamino) -methieno1- erythromycin A EXAMPLE 450 3,5-Dimethyl-isoxazole-4-carboxamide of (11 £ 21 y?, «S) -3-decladinosii-11, 12-dideoxy-6-0-methyl-3-oxo-2,11-foxycarbonyl -f2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 451 4-Oxo-4,5,6,7-tetrahydro-benzofuran-3-carboxamide of (11 £ 21 /? 5) -3- decladinosyl-11,12-d! Deoxy-6-0-methyl- 3-oxo-12,11-fox! Carbon H- (2- (amino) -ethylamino) -methylene] -erythromycin A EXAMPLE 452 3-Amino-pyrazine-2-carboxamide of (11 £ 21 ^) -3-declanedosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 453 Pyrazin-2-carboxamide of (11 £ 21> 5) -3-decladinosl-11,12-dideoxy-6-0-rnethyl-3-oxo-12,11-foxycarbonyl- (2- (amino) ) -ethylamino) -methylene1- erythromycin A EXAMPLE 454 4-Phenyl-n, 2,31-thiadiazole-5-carboxamide of (11 'and, 21?,) -3-declanedosyl-1, 12-dtdeoxy-6-0-rneti-3-oxo-12 , 11 -Foxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 455 5-Methyl-3-methylsulfanyl-isothiazole-carboxamide of (11"21?,) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- ( 2- (amino) -ethalamine) -methylene] -erythromycin A EXAMPLE 456, 6-D -methyl--oxo-4H-pyran-3-carboxamide of (1 ^ 21y?, 5) -3-deciadinosl-1,12-dideoxy-6-0-methyl-3-oxo -12 1-Roxycarbonyl- (2- (amino) -ethylamine) - methyleneol-erythromycin A EXAMPLE 457 decladinosl-11,12-d-deoxy-6-0-methyl-3-oxo-12,11-roxcarbonH- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 458 4-AcetH-3-cyano-5-methyl-pyrrol-2-carboxamide of (11,21? RS? -2- decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12 , 11-roxycarbonyl-f2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 459 4-Methyl-3-oxo-3,4-dihydrc > -2 benzor, 41-thiazine-6-carboxamide of (11521 / ?, 5) -3-declaidinosyl-1, 12-dideoxy-6-0-methyl-3-oxo-12,1-roxycarbonyl- (2- (amino) -etlamino) -methylene-1-erythromycin A EXAMPLE 460 -MetH-imidazor2,1-; fltiazole-5-carboxamide of (11521 / P,) -3-decladinosyl-1,12-dideoxy-6-0-met! L-3-oxo-12,11-roxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 461 - Phenoxy-n-tacinamide of (11"y ^ P ^ - S-decladinosyl-H. ^ - dideoxy-eO-methyl-3-oxo-12,1-hydroxycarbonyl- (2- (amino) - ethylamino) -methylene1- erythromycin A EXAMPLE 462 5-Nitro-1 / indole-2-carboxamide of (11 f21?,) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -et! lamino) - methyleneol-erythromycin A EXAMPLE 463 4,8-D-Hydroxy-quinoline-2-carboxamide of (11 «¾21 ^ 5) -3-decidoxynosyl-, 12-dideoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 464 -Hydrox! -quinoline-4-carboxamide of (11) 21 /?) -3-declaidinosyl-1,12-d-deoxy-6-Q-methyl-3-oxo-12,11-roxycarbon l- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 465 dideox »-6-Q-methyl-3-oxo-12,11-oxocarbonyl- (2- (am!) -ethylamino) -methylene-erythromycin A EXAMPLE 466 Furan-2-yl-oxo-acetamide of (11 ^ 21 ^) -3-decladinosyl-11,12-dideoxy-6,0-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino ) -ethylamino) -methylene1- erythromycin A EXAMPLE 467 2-Am! Non-nicotinamide of (11 £ 21>% S) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12 1-roxycarbonyl- (2- ( amino) -ethylamino) -methylene erythromycin A EXAMPLE 468 1 > ^ Benzotriazole-5-carboxamide of (1 21?,) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino) -ethylamino) - Methyleneol-erythromycin A EXAMPLE 469 3-MetH-furan-2-carboxamide of (11 21y?,. S) -3-deciddnosiM1,12 dideoxy-6-0-methy1-3-oxo-12,11-roxycarbonyl- (2 - (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 470 5-Chloro-1,3-dimetSI-1y ^ pyrazole-4-carboxamide of (11 «¾21 / ?,« S) -3- decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo -12,11 -foxicarbonyl-f2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 471 4-Nitro-1 pyrazole-3-carboxamide of (11 i *, 21 /?) -3-decladinosyl-11, 2-dideoxy-6-0-methyl-3-oxo-12.11-hydroxycarbonyl- (2) - (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 472, 6-Dimethyl-2-oxo-2 ^ pyran-5-carboxamide of (11 ^ 21 g) -3-declanedinosyl-, 12-dideoxy-6-Q-methyl-3-oxo-12, 11-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 473 -Amino-5-chloropyrimidin-4-carboxamide of (11, 21 /?) -3-declanedinos-8,12-dideoxy-6-Q-methyl-3-oxo-2, 1 - | "oxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 474 5-Methyl-1 H3-yrazole-3-carboxamide of (11, 21 → 5, -3-deciadinosyl-11,12-dideoxy-6-0-metii-3-oxo-12,11-roxycarbon! - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 475 1-Methyl-5-oxopyrrolidine-3-carboxamide of (11.¾21 g «í>) -3-decladinosl-11, 12-dideoxy-6-Q-methyl-3-oxo-12 , 1-hydroxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 476 2-Chloro-6-methyl-n-cytanamine of (11 £ 21?,) -3-methsid-1,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2 - (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 477 (4R) -2-Thioxo-1,3-thiazolidin-4-carboxamide of (11,2-dihydroxy) -3-decidinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11- Roxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 478 2,2-Dimethyl-5-oxotetrahydrofuran-3-carboxamide of (11; 21 /? 5) -3-decladinosyl-11, 12-d-deoxy-6-Q-methyl-3-oxo-12, 11-hydroxycarbonyl- (2- (amine) -ethylamino) -methylene-erythromycin A EXAMPLE 479 2.4-DÍQXO-1, 2,3,4-tetrah »dropirimidin-5-carboxamide of (1 S, 2?, S -3-decladinosyl-11, 12-dideoxy-6-Q-metH-3-oxo -12,1-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene] -erythromycin A EXAMPLE 480 2- (Methoxycarbonyl-nicotinamide of (11 ^ yy ^ -S -diddinosyl-ll, ^ -dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) - Methyleneol-erythromycin A EXAMPLE 481 -Methyl-1, 8-naphthyridine-3-carboxamide of (11: 21?, 5) -3-declanedinosl-11,12-dideoxy-6-0-methyl-3-oxo-12,11- foxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 482 2- (Trifluoromet! L) -1,6-naphthridine-3-carboxamide of (11> ¾21?, 5) -3- decladinosyl-11,12-dideoxy-6-Q-nriethyl-3- oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 483 -Benzyl-5-oxo-pyrrolidine-3-carboxamide of (1 '£ 21 /?,. S) -3-decladinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 484 - (Aminocarbonyl) pyrazine-2-carboxamide of (11 *, 21?,> S) -3-decladinosyl 1,12-d-deoxy-6-Q-methyl-3-oxo-12,11-roxycarbonit - (2- (amino) -etHafTiino) - methyleneol-erythromycin A EXAMPLE 485 -Amino-2-methylpyrimidine-5-carboxamide of (11> ¾21> 5) -3-decladinosyl-, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 486 lsoxazole-5-carboxamide of (11"521 and% 5) -3-decladinosyl-1, 12-dideoxy-6- o-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -eti-lamino) -metteneT- erythromycin A EXAMPLE 487 5-Methylisoxazole-3-carboxamide of (5,21 F,) -3-declaidinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-2,11 -foxicarbonyl-f2- (amino) - ethylamino) - methyleneol-erythromycin A EXAMPLE 488 6-Cyanonicotimamide of (11 *, 21 P,) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-2, 1-foxycarbonyl- (2- (amino) -ethylamino) -methylene1- erythromycin A EXAMPLE 489 1-Ethyl-3-methyl-1 > and 3-Irazol-5-carboxamide of (11, 21?,) -3-declaidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (2- (amino) -ethylamino) - Methyleneol-erythromycin A EXAMPLE 490 5-Methylisoxazole-4-carboxamide of (11 «¾21 ^) -3-Declad-Snosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) - ethylamino) - methyleneol-erythromycin A EXAMPLE 491 5-Oxo-l - (thien-2-ylmethyl-pyrroHdin-3-carboxamide of (11.y, 21?, 3-3 dec.) Ad-nosyl-11,12-dideoxy-6- 0-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 492 - (Pyridin-2-ylcarbonyl) -benzamide of (11 ^ 1 / ^ -S -diddinosyl-H, ^ -dideoxy-6-0-methyl-3-oxo-12,11- Roxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 493 1- (2-Furylmethyl) -5-oxopyrrolidine-3-carboxamide of (11.¾21>., S) -3- declined nos-11, 12-dideoxy-6-0-methyl-3-oxo - 2,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 494-f-Methoxycarbonyl) -pi'ridin-2-carboxamide of (11 «¾21 g) -3-decladinosyl-1, 12 .ideoxy-6-0-methyl-3-oxo-12,11-oxoScarbonyl- (2- famino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 495 -f4-Methyl-1,2,3-thiadiazole-5-in-1,3-thiazole-4-carboxamide of (11 S, 2 / ?, Sl-2-decidino! L-11, 12-dideoxy -6-Q-methyl-3-oxo-2,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 496 3-Oxo-2,3-dihydro-1-flndazole-4-carboxamide of (11.R2i?, 5) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12, 11-hydroxycarbonyl-2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 497 -Methyl-1, 6-naphthyridine-3-carboxamide of (11 £ 21 /? 5) -3-decladinosyl-11,12-dideoxy-6-0-rnetyl-3-oxo-12,11-roxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 498 4-Methyl-2-pyridin-4-ii-1,3-t-azole-5-carboxamide of (11.S21 KSl-Z-declaidinosyl-11, 12-dideoxy-6-0-methyl-3- oxo-12,11 -foxicarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 499 4-Methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxamide of (11, 1 », 21?, 5) -3- decladinosyl-11,12-dideoxy-6 -0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 500 dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 501 - (iy- < midazole-1-in-nicotinamide of (11> 9.21> 5) -3-decladinosii-11,12-dideoxy-6-0-methyl-3-oxo- 12,11-foxycarbonyl-f2-famino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 502 5-Methoxy-2- (1,3,5-trimethyl-1 ^ -Izolzol-4 - ») -benzamide of (11 *, 21?,) -3-decladinosyl-1, 12-dideoxy-6 -Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2 (amino) -eti-lamino) -methylene-1-erythromycin A EXAMPLE 503 4-Methyl-2-pyrazyl-2-ii-1,3-thiazo-5-carboxamide of (11 t21?,) -3-decladinosyl-11,12-dideoxy-6-Q-methyl -3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -met-lenol-erythromycin A EXAMPLE 504, 5-Dimethyl-1 > y-pyrrole-3-carboxamide of (11521 /?, ^ - 3-decladinosyl-11,12-d-deoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) - ethylamino) - methyleneol-erythromycin A EXAMPLE 505 4 r (4-Dimethylpyrimidin-2-yl) amino-1-carbonyl > 5-methylisoxazole-3-carboxamide of (11, 21 >?,) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11-oxocarbonyl- (2, - (amino) ^ thylamino) -methylene1-erythromycin A EXAMPLE 506 -Methyl-1 > y-pyrazole-4-carboxamide of (11 ^ 21?,) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) ) - methyleneol-erythromycin A EXAMPLE 507 5-Chloro-1-methi [-3- (trifluoromethyl) -1-phthalimolocarboxamide of (11 ^ 21?, 5) -3-decidnosyl-11,12-dideoxy-6-Q- methyl-3-oxo-12,11-foxycarbonyl- (2- (amine) -ethylamine) -methylene] -ertromycin A EXAMPLE 508 -Pyrimidine-2-Hpiperidine-4-carboxamide of (11.¾21;?,. S) -3-decladinosyl-, 12-d-deoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 509 -Methyl-3- (trifluoromethyl) -1 yypyrazole-4-carboxamide of (11 «S21 / ?, Si-3- dec-N-11,12-diodeoxy-6-Q-methyl-3-oxo-12 , 11-Foxitrocarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 510 (4R) -2-Oxo-1,3-t-azoiidin-4-carboxamide of (11 21 /? 5) -3-decladininosyl-1,2-dideoxy-6-0-methyl-3 -oxo-12,11 -foxicarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 511 (2S) -1-Acetyl-pyrrolidine-2-carboxamide of (11 21?, 6) -3-decladinosyl-1, 12-d-deoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl - (2- (amino) -etHamino) - methyleneol-erythromycin A EXAMPLE 512 5-Nitro-furan-2-carboxamide of (11 ^ 21?, "S) -3-declaidinosyM 1.12- d -deoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 513 1-ethylpyrrolidine-2-carboxamide of (11"£ 21 /?) -3-decladinos-11, 12-dideox! -6-0-met! J-3-oxo-12,11-rox CarboniI- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 514 4-Acet »l-3,5-dimethyl-1 / ¼3-aryl-2-carboxamide of (11 S21>? 5) -3- decladinosyl-1, 12-dideoxy-6-0-methyl- 3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene] -erythromycin A EXAMPLE 515 -Metilnicotinamide of (11, 21 /? -3-decladinosyl-11,12-dideoxy-6-Q-methylo-3-oxo-12,1 -foxicarbonyl-f2- (amino) -ethylamino) -methylene1- erythromycin A EXAMPLE 516 6-MetH-3,4-dihydro-2yy-pyran-5-carboxamide of (11", 21> 5) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3- oxo-12,11-roxycarbonyl-f2- (amine) -ethylamino) -methylene-1-erythromycin A EXAMPLE 517 2J-Dimethylpyrazolori, 5-alpyrmidin-6-carboxamide of (11S, 21β, Sl-3, decidinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -foxicarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 518 -Methyl-1, 2,3-thiadiazole-5-carboxamide of (1, 21?,. S) -3-declanedosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12 , 11-foxycarbonyl- (2- (amino) -eti-amylan) -methylene-l-erythromycin A EXAMPLE 519 4- (Trifluoromethyl) -nicotinamide of (1U ^ 1;) -3-decladinosyl-11.12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -eti-arnino) - Methyleneol-erythromycin A EXAMPLE 520 4-Oxo-4 > y-Chromen-2-carboxamide of (H ^ P ^ -S-decladinosyl-H, ^ - dideoxy-6-0-metH-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino Methyleneol-erythromycin A EXAMPLE 521 -Amino-1 / y-pyrazole-4-carboxamide of (11 ^ l ^ -Sj-S-decladinosyl-H, ^ -d-deoxy-6-0-methyl-3-oxo-12.11-roxycarbon! - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 522 2-Chloronicotinamide of (11"R21?, 5) -3-Re-decidinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-xylcarbonyl- (2- (amino) -ethylamide no) -methylene1- erythromycin A EXAMPLE 523 2-Oxo-2 / y-pyran-5-carboxamide of (11"?, 21?, > -3-dedadinosyl- 1.12-d-deoxy-6-0-methyl-3-oxo-12,11 -roxycarbonH- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 524 Furan-3-carboxamide of (11 ^ and ^ -S -diddinosyl-ll. ^ - dideoxy-eO-methyl-3-oxo-12,1 -fox! Carbonyl- (2- (amino) -ethylamino ) -methylene1- erythromycin A EXAMPLE 525 1,2,3-Tiadiazole-4-carboxamide of (H ^ ip ^ -S-decladinosyl-H, ^ -d-deoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl - (2- (amino) -ethylamino) methylene-erythromycin A EXAMPLE 526 1,5-Dimethyl-1 ^ ¾-irazole-3-carboxamide of (11 5 *, 21 / P, S) -3-declanedinosH-1, 12-dideoxy-6-Q-methyl-3-oxo -12,11-Foxcarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 527 y ^ Pyrazole-4-carboxamide of (11"?, 21 /? 5) -3-decladinosyl-1, 12-dideoxy-6-Q-methyI-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene "l-erythromycin A EXAMPLE 528 -Met »-4-oxo-4HH3¡ridon, 2-a1p! R! Midin-3-carboxamide of (11 21 ^^ -3-decidnosyl-11, 12-dideoxy-6-Q-methyl-3- oxo-12,11 -foxicarbonyl- (2- (amine-ethylamine) -methylene-erythromycin A EXAMPLE 529, 6-Dimethoxynicotinamide of (11 21 / P,) -3-decladinosyl-11,1-dideoxy-6,0-methyl-3-oxo-2,11-hydroxycarbonyl- (2- (aniin) -ethylamino) -methylene1- erStromycin A EXAMPLE 530 4-Chloro-1,3-dimethyl-1 y¾-irazoIor3,4-blpyrdin-5-carboxamide of (11 £ 21?,. Fl-3-decidnosyl-11.12-d-deoxy-6-Q -metoly-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 531 2-Meti-Nicotinamida of (11 2 y 5, 5) -3-decla-dinosyl-11,12-dideoxy-6-O-methyl-3-oxo-12,11-dioxycarbonyl- (2- (amino) -ethylamino ) -methyl-ene-erythromycin A EXAMPLE 532 5-Amino-2,6-dioxo-1, 2,3,6-tetrahydropyrimidine-4-carboxamide of (11 S, 2"\?,. S) -3-decladinosyl-11,12-d-deoxy -6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 533 -Hydroxy-3- (morpholin-4-ylmethyl) -benzamide of (11 ^ 1 / ^ -S -diddlynosyl-1,12-dideoxy-6-Q-methyl-3-oxo-2,11-hydroxycarbon) l- (2- (amine) -ethylamino) -methyleneol-erythromycin A EXAMPLE 534 dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 535 6- Oxo-l, 4,5,6-tetrahydropyridazine-3-carboxamide of (11 & 21 /?) -3-deciddinosi-11, 12-dideoxy-6-0-methyl-3- oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 536 / pir pyrrole-2-carboxamide of (11"¾21y?) -3-methionyl-11,12-d-deoxy-6-methyl-3-oxo-12,11-hydroxycarbonyl-2 - (amino) -ethylamino) -methylene1- erythromycin A EXAMPLE 537 .2-Dimet »l-4-oxo-3,4-dlhydro-2 ^ pyran-6-carboxamide of (11 *, 21 /? 5> -3- decladinosyl-11,2-dideoxy-6) -0-methyl-3-oxo-12,11 -foxicarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 538 1-Methyl-1 pyrrole-2-carboxamide of (11) 21 > ?,) -3-decipadsil-11,12-dideoxy-6-methyl-3-oxo-12,11-roxycarbonyl- (2-ylamino) -ethylamino) methyleneol-erythromycin A EXAMPLE 539 2,3-Dihydro-1,4-benzodioxin-2-carboxamide of (11"£ 21?," Fl-3-decidinosyl-11, 12-dideoxy-6-Q-metH-3-oxo-12, 1-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 540, 4-Dimethyl-1, 3-thiazole-5-carboxamide of (11 ^ lg ^ -S -diddinosyl-H, ^ -dideoxy-6-0-methyl-3-oxo-12- [oxycarbonyl- (2 - (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 541 1-Met! [-1,2,5,6-tetrahydropyridine-3-carboxamide of (11 *, 21?, 5¾-3- decidines H-1, 12-dideox! -6-Q-methyl- 3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 542 1-Oxi-pyridine-2-carboxamide of (11.S21 / ?, 5) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl-f2- famino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 543 -Acetylpiperidine-4-carboxamide of (11 ^^ lg ^ -S -diddinosyl-H, ^ -dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino)) -ethylamino) - methyleneol-erythromycin A EXAMPLE 544 Tetrahydrofuran-3-carboxamide of (11 ^ 21y?) -3-declanedinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino ) - methylenol-erithromycin A EXAMPLE 545 S) -5-Oxopyrrolidine-2-carboxamide of (11 £ 21?,) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 546 -Hydroxynicotinamide of 11 11 P 1 -S-decladinosyl-H 4 -dideox S -O-methyl-3-oxo-12,11-foxycarbonyl- (2-famino) -ethylamino) -methylene V erythromycin A EXAMPLE 547 3,6-Dichloropyridazine-4-carboxamide of (H ^ I ^^ - S-decladinosyl-H, ^ -dideoxy-6-methyl-3-oxo-12 1-roxycarbonyl-f2-famino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 548 1-Et! L-7-methyl-4-oxo-1,4-dihydro-1, 8-naphthyridine-3-carboxamide of (11 £ 21?, 5) -3-declaidinosi-11, 12 -dideoxy-6-Q-methyl-3-oxo-12,11 - [oxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 549 Furan-2-carboxamide of (11 S21> 5) -3 iecladinosiM1, 12-d, deoxo-6-0-metH-3-oxo-12, 11 -foxicarbon, > - (2- (amino) -eti > amlno) -methylene] - erythromycin A EXAMPLE 550 Pyridine-2-carboxamide of (11, 21y?) -3-Redenedinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino) -ethylamino ) -methylene] - erythromycin A EXAMPLE 551 Nicotinamide of (11 ^; 21 g5) -3-declanedinosl-1, 12-dideoxy-6-0-metH-3-oxo-12 1 -roxycarbonyl- (2-amino) -tylamino) -methylene1- erythromycin A EXAMPLE 552 Tetrahydrofuran-2-carboxamide of (11 ^, 21 > ^^) - 3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-Foxicarbonyl- (2- (amino) ) -ethylamino) - methyleneol-erythromycin A EXAMPLE 553 2-Methyl-furan-3-carboxamide of (11 ^ 21 /?) -3-decladinosyl-1, 12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 554 (2 > fl-Tetrahydrofuran-2-carboxamide of (11 ^ l ^^ - S-decladinosyl-H, ^ -didesoxy-6-0-methyl-3-oxo-12,1-hydroxycarbonyl- (2) - (amino) -ethylamino) - methylenol-erythromycin A EXAMPLE 555 2- (5-Oxopyrrolidin-2-ylsulfanyl) -benzamide of (11 ^ l P ^ -S -diddinosyl- 1, 12-dideoxy-6-Q-methyl-3-oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 556 1-Allyl-2-oxo-1,2-dihydropyridine-3-carboxamide of (11521?,) -3-declanedinosn-1,12-dideoxy-6-Q-methyl-3-oxo-12, 11-Roxycarbonyl- (2- (amino) -ethylamino) -methylene-1-erythromycin A EXAMPLE 557 2-Methyl-4- (trifluoromethyl) -1,3-thiazole-5-carboxamide of (11 ^ 21?, "Sl-3-decidinosyl-1, 12-dideoxy-6-0-methyl-3-oxo -12,11 -foxicarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 558 6-Hydroxy-1-methyl-2-oxo-1,2-dihydropyrimidine-4-carboxamide of (11, S21> and, 5) -3-declanedinosyl-11, 12-d-deoxy-6 -Q-methyI-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamine) -metHeno1-erythromycin A EXAMPLE 559 3-Methyloxazole-4-carboxamide of (11β: 21y7, ^ -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbonH- ( 2- (amino) -ethylamine) - methyleneol-erythromycin A EXAMPLE 560-Methoxy-1,3-oxazole-2-carboxamide of (11 ^ lg ^ -S -dididinosyl-H, ^ -dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- (2- (amine) -eti-amino) - methyleneol-erythromycin A EXAMPLE 561 2-r6- (Acetylamino) -pyridin-3-ylsulfan-n-nicotinamide of (11 «g, 21 /?,. S) -3-decladinosyl-11, 12-dideoxy-6-Q-methyl-3- oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 562 - (4-Methylpiperazin-1-yl) -3-nitro-benzamide of (11. £ 21 /?) -3-decladinosyl-11 l-12-dideoxy-6-Q-methyl-3-oxo-12, 11 - [oxocarbonyl- (2- (amine) -ethylamino) -methylene] -ertromethin A EXAMPLE 563 4-lsopropyl-1, 2,3-thiadiazole-5-carboxamide of (11 ^ 2iy?) -3-decladinosyl-11112-dideoxy-6-0-methyl-3-oxo-12, 1- [oxycarbonyl - (2- (amino) -ethylamine) -methylene-erythromycin A EXAMPLE 564 3-Oxo-2-phenyl-2,3-dihydropyridazine-4-carboxamide of (.R21?, S] -3- declade-1-11,12-d-deoxy-6 0-metM-3-oxo-12,11-roxycarbonrl- (2- (amino) -ethylamino) -metholene-1-erithromycin A EXAMPLE 565 5-Bromo-2-oxo-1,2-dihydropyridine-3-carboxamide of (11 ^ 21 ^) -3- decladinosyl-11, 12-dideoxy-6-Q-methyl-3-oxo-12,11 - [OxicarbonH- (2- (amino) -ethylamino) -methieno] -erythromycin A EXAMPLE 566 - (Methoxycarbonylopiperidine-4-carboxamide of (11 ^ *, 21>), 3-methsidi-1,12-dideso i-6-0-met ^? - 3-oxo-2? 11-Gox ^ carbonH-f2- (a? tinoin) -etHamino) methyleneol-erythromycin A EXAMPLE 567 1- (6-Chloropyridazin-3-inpiperidm-4-carboxamide of (11 S, 21 /? SI-3-decidinosyl-11,12-dideoxy-6-Q-methyl -3-oxo-2,11 -foxicarbonyl- (2- (amino) -ethylamino) -methyl-ene-erythromycin A EXAMPLE 568 -Chloro-6-oxo-1-phenyl-1,6-dihydropyridazine-3-carboxarnide of (11 ^ 21?,) - 3-decladinosyl-11, 12-d-deoxy-6-Q-methyl-3 -oxo-12,11-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythrotnicin A EXAMPLE 569 1- (3-Chlorophenyl) -4-methoxy-6-oxo-1,6-dihydropyridazine-3-carboxamide (11 £ 2 / ?,) -3-Decladinosyl-11,12-d-Deoxy-6-Q-methyl-3-oxo-12,11 - [oxycarbon] -1- (2- (amino) -ethylamino) -methylene1- Erythromycin A EXAMPLE 570 (1-Methyl-4-nitro-1 > yplrazole-5-yl) -acetamide from (11 S21 /?) -3-declanedosyl-11,12-d-deoxy-6-Q- methyl-3-oxo-12,11 -rox »carbonyl- (2- (amino) -etHamino) - methylaenol-erythromycin A EXAMPLE 571 (1, 3-Dimet »l-2,6-dioxo-2,3,6,7-tetrahydro-1-purin-8-yl) -acetamide from (11 £ 21?,) -3-decladinosil -11, 12-dideoxy-6-0-methyl-3-oxo-12,11-foxcarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin A EXAMPLE 572 5-Oxo-4,5-dihydrodrofuran-3-carboxamide of (11, 21?,) -3-decladinosyl-11,12-d-deoxy-6-0-methyl-3-oxo-12,11-oxycarbonyl - (2- (amino) -et! Larnino) methyleneol-erythromycin A EXAMPLE 573 2 / ^ 4) -4- (Acetyloxy) -1,3-oxathiolan-2-carboxamide of (11 £ 21 5) -3- decladinosyl-11, 2-d-deoxy-6-Q-methyl-3 -oxo-12,11-hydroxycarbonyl- (2 (amino) -ethylamino) -methylene-1-er8tromethycin A EXAMPLE 574 -Hydroxyisonicotinamide of (11,21 ^^^ -s-decladinosyl-l 1,12-dideoxy-6,0-rnethyl-3-oxo-2,11-roxycarbonyl- (2- (amino) -ethylamino) - methylene - erythromycin A EXAMPLE 575 3-Hydroxypyridine-2-carboxamide of (11 «¾21y¾) -3-deciadinosi 1,12-d'deoxy-6-0-metii-3-oxo-12,11-foxycarbonyl- (2- (amino) - ethylammon) - methylenol-entrromicin A EXAMPLE 576 -Hydroxinicotinamide of (11 ^ 21 ^) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-foxycarbonyl- (2- (amino) -ethylamino) -methylene-erythromycin TO EXAMPLE 577 -Hydroxy-4-oxo-4yy-chromen-2-carboxamide of (11, 21 / P, 5) -3-decladinosyl-1, 12-dideoxy-6-Q-methyl-3-oxo-12,11 -roxycarbonyl- (2- (amino) -etiaminoy methiienol-erythromycin A EXAMPLE 578 1 -Oxy-nicotinamide of (11. £ 21?,) -3-decladinosi 1, 12-dideoxy-6-Q-G? 6? 1-3-? ? -12,11-G ???? 3 ^ ???? - (2- (3 ?????) - 6 ??? 3G ????) - ?? 6 ??? 6 ?? ? - erythromycin A EXAMPLE 579 lndol-2-carboxamide of (11.9.21 / ?, «S) -3-decladinosyl-11,12-dideoxy-6--0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino ) -ethylamino) -metholene-erythromycin A EXAMPLE 580-Methoxy-1 > Α-phenyl-2-carboxamide of (11 S, 2"\ /, 5) -3-decidino-l-11,12-dideoxy-6-Q-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 581 -chloro-4-oxo-4 > y-Chromen-2-carboxamide of (11 £ 21?,. S) -3-Decladinosyl-1, 12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl- - (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 582 Quinoline-2-carboxamide of (11 ^ 21 ^^) - 3-Redenedinosyl-11,12-dideoxy-6,0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -ethylamino ) -methylene1- erythromycin A EXAMPLE 583-Hydroxy-6-methoxyquinoline-2-carboxamide of (11 ^ Iv ^^ - S-decladinosyl-11,12-dideoxy-6-0-metH-3-oxo-12 1-roxycarbonH- (2- ( amino) -etHamino) - methyleneol-erythromycin A EXAMPLE 584 4-Methyl-3-oxo-3,4-dihydroquinoxaline-2-carboxamide of (1 Sr 2"\ / ?, Si-3-decladinosyl-11,12-dideoxy-6-0-metH-3-oxo- 2111-Roxycarbonyl- (2"(amino) -ethylamino) -methylene] -erythromycin A EXAMPLE 585 4- (2-Hydroxyethyl) -3-oxo-3,4-dihydroquinol-2-carboxamide (1 → 21 >?,. Fl-3-decidnosyl-11,12-dideoxy-6-Q-methyl-3-oxo-12,1-hydroxycarbonyl- (2- (amino) -ethylamino) - methylenol-erythromycin A EXAMPLE 586-Methoxyquinoline-2-carboxamide of (11 *, 21? F) -3-declanedinosi 1,12-dideoxy-6-0-methyl-3-oxo-12,11-foxycarbonyl- ( 2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 587 1-Benzofuran-2-carboxamide of (11 ¾21?,) -3-decladinosyl-11,12- d -deoxy-6-0-methyl-3-oxo-12,11-roxycarbonyl- (2- (amino) -eti > amino) - methyleneol-erythromycin A EXAMPLE 588 6-Ethyl-5-oxothiomorpholine-3-carboxamide of (11 ^ 21 ^) -3-methylene-1, 12-dideoxy-6-0-methyl-3-oxo-12,11-hydroxycarbonyl - (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 589 -Chloro-1-oxy-nicotinamide of (1, 21 and?, ^) - 3-declaidinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-oxycarbonyl- (2- ( amino) - ^ tilamino) -iTiethylene1- erythromycin A EXAMPLE 590 Oxo- (thien-2-in-acetamide of (11 ^ l P ^ -S -diddinosyl-H. ^ - dideoxy-S- 0-methyl-3-oxo-12,11-hydroxycarbonyl- (2 - (amino) -ethylamino) -methylene1- erythromycin A EXAMPLE 591 Oxo- (phenyl) -acetamide of (11 ^ P ^ -S -diddinosyl-l ^ -dideoxy-eO-methyl-3-oxo-12,11-roxycarbonyl- (2- (amine) -ethylamino) -methylene - erythromycin A EXAMPLE 592 3- (2-Nitrophenyl) -2-oxo-propionamide of (11: 21 /?) -3-decladinosyl-11,12-dideoxy-6-Q-methyl-3-oxo-2,1-hydroxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 593 - (1yy-Jndol-3-yl) -2-oxo-proponamide of (11 *, 21?,) -3-declanedinosyl-1, 12-dideoxy-6-0-methyl-3-oxo- 12,11-Roxycarbonyl- (2- (amino) -eti-amino) -methylene-erythromycin A EXAMPLE 594 -Oxo-3-phenyl-prop-onamide of (11 S, 2"? 5) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11-roxycarbon L- (2- (amino) -ethylamino) -methylene1- erythromycin A EXAMPLE 595 (2E) -3- (1 / Elmidazol-4-yl) -acrylamide of (11. £ 21 g) -3-declanedinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12, 11-Roxycarbonyl- (2- (amino) -ethylamino) -methyleneol-erythromycin A EXAMPLE 596 (2E) -3- (1 ^ lndol-3-i) -acrylamide of (11; 21 g) -3-decladinosyl-11,12-dideoxy-6-0-methyl-3-oxo-12,11 -roxycarbonyl- (2- (amino) -etüamino) - methyleneol-erythromycin A EXAMPLE 597 3- (1,3-Benzod¡oxo [-5-yl] prop-2-inamide of (11 *, 21/7,) -3-decladinosyl-, 12-dideoxyU6-0-methyl-3-oxo-12 , 11-Roxycarbonyl- (2- (amino) -ethylamino) - methyleneol-erythromycin A EXAMPLE 598 (2E) -3-Qulnolin-3-yl-acrylamide of (11, 21 /? 5) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12, 11-Roxycarbonyl- (2-famino) -ethylamino) -methylene-erythromycin A EXAMPLE 599 (2E) -3-Quinolin-2-yl-acrylamide of f 11521 and?, 5) -3-declanedinosl-11, 12-dideoxy-6-0-methyl-3-oxo-12,11 ox »Carbonif- (2-famino) -etlarnino) - methyleneol-erythromycin A EXAMPLE 600 (Quinoxalin-2-ylsulfanyl) -acetamide of (11521?,) -3-decladinosyl-11, 2-dideoxy-6-Q-rriethyl-3-oxo-12,11-roxycarbonyl- (2- (amino)) -ethylamino) - methyleneol-erythromycin A EXAMPLE 601 r5- (5-Nitro-furan-2-yl) -ri, 3,41-oxadiazol-2-ylsulfanin-acetamide of (11521?, 5 »-3-declanedinosi. 12-dideoxy-6-Q-methyl-3 -oxo-12.11 - roxycarbonyl- (2- (amino) -eti-lamino) -metholene-erythromycin A Examples 427-601 were obtained starting from example 13 (5 mg), following the same procedure reported for example 426.

The name and amount of the starting material (ie, carboxylic acid), and the LC / MS analysis (retention time and m / z) of examples 427-601, are reported in table 6.

TABLE 6 TABLE 6 (CONTINUATION) 2-Pirazin-2-yl-thiazole-4- 433 1.5 5.92 859 carboxylic acid Acid 3-Methyl-2-oxo-1, 2- 434 1.5 5.45 855 dihydro-quinoline-4-carboxylic acid Acid 2-Methyl-imidazo [1, 2, - 435 1 .3 5.64 828 a p i ri di? -3-carboxylic acid 4-Methoxy-1,3-dimethyl-1 H-436 pyrazolo [3,4-Z > ] pyridine-5- 1.7 5.7 873 carboxylic acid 3-Methyl-5- (4-methyl-437 [1, 2,3-thiadiazol-5-yl) -isoxazole- 1.7 6.68 877 4-carboxylic acid 4-Acetyl-1-methyl-1 - 438 acid 1.2 5.56 819 pyrrole-2-carboxy acid Acid 6- [1, 2,4] Triazol-1 -il- 439 1.4 5.52 842 nicotinic 440 Isonicotinic Acid 0.9 5.22 775 Acid 5-Oxo-2,3-dihydro-5 H- 441 t¡azolo [3,2-¿?] Pyrimidin-6- 1 .5 5.35 850 carboxylic acid Acid 5-Nitro-1 / pyrazole-3- 442 1 .2 5.44 809 carboxylic acid 43 2-Methylsulfanyl-nicotinic acid 1.3 6.07 821 7-Hydroxy-2-oxo-2/44 acid 1.5 5.7 856 chromen-3-carboxylic acid TABLE 6 (CONTINUED) 445 Cinolin-4-carboxylic acid 1.3 5.7 826 446 6-Amino-nicotinic acid 1.0 5.1 790 Acid 1-Methyl-5-nitro-1 / ¿447 1.3 6 823 pyrazoi-4-carboxylic acid 4,7-Dimethyl-pyrazolo [5,1-448 1.4 6.4 844, 2,4] triazine-3-carboxylic acid 449 2-Methoxy-nicotinic acid 1.1 6.2 805 3,5-Dimetii-isoxazole-4- 450 1.1 6 793 carboxylic acid 4-0x0-4,5,6,7-451 tetrahydro-benzofuran-3- 1.3 6.2 832 carboxylic acid Acid 3-Amino-pirazin-2- 452 1.0 5.9 791 carboxíüco 453 Pirazin-2-carboxylic acid 0.9 5.6 776 4-Phenyl- [1,2,3] thiadiazole-454 1.5 7.1 858 5-carboxylic acid Acid 5-Methyl-3-metilsulfanil- 455 1.4 6.7 841 isothiazole-4-carboxylic acid 2,6-Dimethyl-4-oxo-4 H-456 acid 1.3 5.5 820 pyran-3-carboxylic acid TABLE 6 (CONTINUED) Acid 1-Oxo-1, 2-dihydro- 457 1.4 5.5 841 soquinolin-4-carboxylic acid 4-Acetyl-3-cyano-5-methyl-458 acid 1.4 5.8 844 1 // pyrrole-2-carboxylic acid 4-Methyl-3-oxo-3,4- 459 dihydro-2-benzo [1,4] thiazine-6- 1.7 6.2-875 carboxylic acid 6-Metii-imidazo [2.1- 460 1.4 5.8 834] thiazole-5-carboxylic acid 461 2-Phenoxy nicotinic acid 1.6 6.9 867 5-Nitro-1 indole-2- 462 1 .5 6.9 858 carboxylic acid 4,8-Dihydroxy-quinoiin-2- 463 1 .5 5.6 857 carboxylic acid 2-Hydroxy-quinoline-4,464 1,4,5,841 carboxylic acid Acid (1 / lndol-3-yl) -oxo- 465 1.4 6.7 841 acetic acid 466 Furan-2-ü-oxo-acetic acid 1.0 6.3 792 467 2-Amino-Nitinic Acid 1.0 9.1 790 Acid 1 Benzotriazoi-S-68 1.2 6.9 815 carboxylic BOX 6 (CONTINUED) 3-Methyl-furan-2- 469 1.0 1 1 778 carboxylic acid Acid 5-Chloro-1,3-dimethyl-1/470 1.3 5.7 826 pyrazole-4-carboxylic acid 4-Nitro-1 / pyrazole-3- 471 1.2 5.40 809 carboxylic acid 4,6-Dimethyl-2-oxo-2 acid 5.48 472 1.3 820 pyran-5-carboxylic acid 5.89 Acid 2-Amino-5-473 1.3 5.49 825 chloropyrimidine-4-carboxylic acid 5-Methyl-1 / -pyrazole-3- 474 0.9 5.16 778 carboxylic acid 1-Methyl-5-oxopyrrolidin-475 1.1 4.67 795 3-carboxylic acid Acid 2-Chloro-6- 476 1.3 5.75 823 Methylnicotinic acid Acid (4R) -2-Thioxo-1, 3- 477 1 .2 5.72 815 thiazolidin-4-carboxylic acid Acid 2,2-D-methyl-5-78 oxotetrahydrofuran-3- 1.2 5.66 810 carboxylic acid 2,4-Dioxo-1, 2,3,4-79 tetrahydropyrimidin-5- 1.3 4.70 808 carboxylic acid 2- (Exoxycarbonyl) - 80 1.4 5.79 833 Nicotinic Acid TABLE 6 (CONTINUED) 2-Methyl-1, 8-naphthyridine-3-481 1.4 5.05 840 carboxylic acid 2- (Trifluoromethyl) -1, 6-482 1.8 6.15 894 naphthyridine-3-carboxylic acid Acid 1-Benzyl-5-oxopyrrolidin-483 1.6 5.93 871 3-carboxylic acid 3-484 (Aminocarbonyl) pyrazin-2- 1.2 4.66 819 carboxylic acid 4-Amino-2- 485 1.1 4.98 805 methylpyrimidine-5-carboxylic acid 4. 46 486 lsoxazole-5-carboxylic acid 0.8 765 5.55 5-Methylisoxazole-3-487 0.9 5.98 779 carboxylic acid 88 6-Cyanonicotinic acid 1.1 5.90 800 1-Ethyl-3-methyl-1 / V-89 acid 1.2 6.05 806 pyrazole-5-carboxylic acid 5-Methyl isoxazole-4- 90 0.9 4.35 779 carboxylic acid Acid 5-Oxo-l - (thien-2-ylmethyl) - 91 1.7 5.79 877 pyrroline-3-carboxylic acid 2- (Pyridin-2-ylcarbonyl) - 6.18 92 1.7 benzoic acid 879 6.44 TABLE 6 (CONTINUED) Acid 1- (2-Furilmetl) -5- 493 1.6 5.55 861 oxopyrrolidine-3-carboxylic acid 5- (Methoxycarbonyl) - 494 1 .4 6.24 833 pyridine-2-carboxylic acid 2- (4-Methyl-1, 2,3-495 thiadiazole-5-ii) -1,3-thiazole-4-7.635-879 carboxylic acid Acid 3-Oxo-2,3-dihydro-1 - 496 1.3 5.63 830 indazol-4-carboxylic acid Acid 2-Methyl-1, 6-naphthyridin-3- 497 1.4 5.19 840 carboxylic acid 4-Methyl-2-pyridin-4-yl-1, 3- 498 1.6, 5.94, 872 thiazole-5-carboxylic acid 4-Methyl-2-pyridin-3-i! -1, 3-499 1.6 5.94 872 thiazole-5-carboxylic acid Acid chlorhydrate 4- 500 1.9 5.68 873 (morpholin-4-ylmethyl) -benzoic acid Acid 6- (1 // - lmidazo! -1 -il) - 501 1 .4 5.40 841 nicotinic 5-Methoxy-2- (1, 3,5-502 trimethyl-1 // - pyrazol-4-yl) - 1.9 6.13 912 benzoic acid 4-Methyl-2-pyrazin-2-yl-503-acid 1.7 6.18 873 1, 3-thiazole-5-carboxylic acid Acid 2,5-Dimethyl-1 iDrol-3-504 1.0 5.64 791 carboxylic BOX 6 (CONTINUED) Acid 4-. { [(4,6-Dimethylpyrimidin-505 2-yl) amino] carbonyl} -5- 2.1 6.49 928 methyl isoxazole-3-carboxylic acid 1-Methyl-1-pyrazole-4- 506 0.9 5.03 778 carboxylic acid 5-Chloro-1-methyl-3-507 (trifluoromethyl) -l / -pyrazol-4- 1.7 6.57 880 carboxylic acid 1-Pyrimidin-2-ylpiperidine- 508 1.5 5.89 859 4-carboxylic acid Acid 1 -Methyl-3- (tnfluoromethyl) - 509 1.4 6.02 846 1 -pyrazole-4-carboxylic acid Acid (4R) -2-Oxo-1, 3- 510 1 .1 5.11 799 thiazolidin-4-carboxylic acid Acid (2S) -1 -AcetiIpirroIidin-2- 51 1 1.2 4.95 809 carboxylic acid 5-Nitro-furan-2- 512 1 .2 6.18 809 carboxylic acid Acid 1-Methylpyrrolidin-2- 513 1.1 5.28 781 carboxylic acid Acid 4-Acetyl-3,5-dimethyl-1 - 514 1.4 5.63 833 pyrrole-2-carboxylic acid 515 6-Methylnicotinic Acid 1.0 5.31 789 6-Methyl-3,4-dihydro-2 // - 16 1 .1 5.95 794 pyran-5-carboxylic acid TABLE 6 (CONTINUED) Acid 2,7-Dimethylpyrazolo [1, 5- 517 1.4 5.63 843 a] pyrmidine-6-carboxylic acid 4-Met l-1, 2,3-thiadiazol-5- 518 1 .1 6.01 796 carboxylic acid 4- (Trifluoromethyl) - 519 1.4 5.98 843 nicotinic acid Acid 4-0x0-4 H-chromen-2- 520 1.4 6.2 842 carboxylic 5-Amino-1 / -pyrazol-4- 521 0.9 5.1 779 carboxylic acid 522 2-Cloronicotinic Acid 1.2 5.7 809 2-Oxo-2-pyran-5- 5.4 523 1.0 792 carboxylic acid 5.8 524 Furan-3-carboxylic acid 0.8 5.9 764 Acid 1,2,3-thiadiazol-4- 525 1.0 5.8 782 carboxylic acid 1, 5-Dimethyl-1 / -pyrazol- 526 1.0 5.6 792 3-carboxylic acid 527 Pyrazole-4-carboxylic acid 0.8 4.5 764 Acid 8-Methyl-4-oxo-4 H-528 pyrido [, 2-a] pyrimidine-3- 1.5 5.7 856 carboxylic BOX 6 (CONTINUED) 529 2,6-Dimethoxynicotinic acid 1.4 6.9 835 Acid 4-Chloro-1,3-dimetii-1 - 530 pyrazolo [3,4-b] pyridin-5- 1.7 6.2-877 carboxylic acid 531 2-Methylnicotinic Acid 1.0 5.4 781 5-Amino-2,6-dioxo-532 1, 2,3,6-tetrahydropyrimidin-4- 1.3 4.8 823 carboxylic acid 4-Hydroxy-3- (morfoiin-4- 533 1.9 6.0 889 ilmethyl) -benzoic acid 5-Methylpyrazine-2- 534 1.0 5.8 790 carboxylic acid Acid 6-0x0-1, 4,5,6- 535 tetrahydropyridazin-3- 1.1 5.1 794 carboxylic acid 536 1-Pyrrole-2-carboxylic acid 0.8 5.9 763 Acid 2,2-Dimethyl-4-oxo-3,4- 537 1.3 6.0 822 dihydro-2 / -pyran-6-carboxylic acid Acid 1 -Methyl-1 / -pyrrol-2- 538 0.9 6.3 777 carboxylic acid Acid 2,3-Dihydro-1, 4- 539 1.3 6.9 832 benzodioxin-2-carboxylic acid 2,4-Dimethyl-1,3-thiazole-5-40 acid 1.2 5.8 809 carboxylic acid TABLE 6 (CONTINUED) Acid 1-Methyl-1 .2-5.6- 541 1 .3 4.9 793 tetrahydropyridine-3-carboxylic acid 1-Oxi-pyridin-2- 542 1 .0 5.3 791 carboxylic acid Acid 1-Acetylpiperidin-4- 543 1.3 5.1 823 carboxylic acid Tetrahydrofuran-3- 544 0.9 5.6 768 carboxylic acid Acid (2S) -5-Oxopyrrolidin-2- 545 1.0 4.7 781 carboxylic acid 546 6-Hydroxynicotinic acid 1.0 4.6 / 4.8 791 3,6-Dichloropyridazine-4- 547 1.4 6.4-844 carboxylic acid 1-Ethyl-7-methyl-4-oxo-1, 4- 548-dydro-1, 8-naphthyridin-3- 1.7 6.7 884 carboxylic acid 549 Furan-2-carboxylic acid 0.8 5.8 764 550 Pyridine-2-carboxylic acid 0.9 6.0 775 51 Nicotinic acid 0.9 5.3 775 Acid Tetrahydrofuran-2- 52 0.9 5.6 768 carboxylic BOX 6 (CONTINUED) 2-Methyl-furan-3- 553 0.9 6.3 778 carboxylic acid Acid (2R) -Tetrahydrofuran-2- 554 0.9 5.6 768 carboxylic 2- (5-Oxopyrrolidin-2- 5.7 555 1.8 889 sulfosyl) -benzoic acid 6.1 1-Allyl-2-oxo-1, 2- 556 1 .3 6.0 831 dihydropyridine-3-carboxylic acid Acid 2-Methyl-4- (trifluoromethyl) - 557 1.6 6.7 863 1, 3-thiazole-5-carboxylic acid 6-Hydroxy-1-methyl-2-oxo-558 1,2-dihydropyrimidin-4- 1 .3 5.1 822 carboxylic acid 3-Methylisoxazole-4- 559 0.9-5.9 779 carboxylic acid 5-Methoxy-, 3-oxazole-2- 5.4 560 1 .1 795 carboxylic acid 5.8 Acid 2- [6- (Acetylamino) - 561 2.2 5.9 941 pyridin-3-ylsulfanyl] -nicotinic acid 4- (4-Methylpiperazin-1-iI) - 562 2.0 6.0 917 3-nitro-benzoic acid 4-lsopropyl-1, 2,3- 63 1.3-thiadiazole-5-carboxylic acid Acid 3-Oxo-2-phenyl-2,3- 64 1.6 6.7 868 dihydropyridazine-4-carboxylate TABLE 6 (CONTINUED) Acid 5-Bromo-2-oxo-1, 2- 565 1.6 5.6 869 dihydropyridine-3-carboxylic acid Acid 1- 566 (methoxycarbonyl) piperidin-4- 1.4 5.6 839 carboxylic acid Acid 1- (6-Chloropyridazine-3,667 1.8 6.0 893 il) piperidine-4-carboxylic acid Acid 4-Chloro-6-oxo-1-phenyl-6.2 568 1, 6-dihydropyridazin-3- 1.9 902 6.6 carboxylic acid 1- (3-Chlorophenyl) -4- 6.2 569 methoxy-6-oxo-1, 6- 2.1 932 6.5 dihydropyridazine-3-carboxylic acid Acid (1-Methyl-4-nitro-1 - 570 1 .4 5.9 837 pyrazol-5-yl) -acetic acid Acid (1,3-dimethyl-2,6-dioxo-571 2,3,6,7-tetrahydro-1 / -purin-8- 1.8 5.2 890 il) -acetic 5-Oxo-4,5-dihydrofuran-572 1.0 7.2 780 3-carboxylic acid Acid (2R, 4S) -4- (Acetyloxy) - 573 1.4 6.0 844 1, 3-oxathiolan-2-carboxylic acid 574 3-Hydroxyisonicotinic acid 1 .0 5.2 791 Acid 3-Hydroxypyridin-2- 6.7 575 1.0 791 carboxylic 7.1 76 2-Hydroxynicotinic acid 1 .0 5.0 791 TABLE 6 (CONTINUED) 7-Hydroxy-4-oxo-4 - 577 1 .5 5.4 858 chromen-2-carboxylic acid 578 1-Oxi-nicotinic acid 1.0 4.8 791 579 1 lndol-2-carboxylic acid 1.2 6.8 813 Acid 5-Methoxy-1 // Hndol-2- 580 1.4 6.7 843 carboxíüco 6-chloro-4-oxo-4 / - 581 1.7 7.0 876 chromen-2-carboxylic acid 582 Quinolin-2-carboxylic acid 1.3 7.1 825 4-Hydroxy-6- 583 1.6 5.7 871 methoxyquinoline-2-carboxylic acid 4-Methyl-3-oxo-3,4- 584 1 .5 5.8 856 dihydroquinoxaline-2-carboxylic acid 4- (2-Hydroxyethyl) -3-oxo-585 3,4-dihydroquinoxaiin-2- 1.7 5.3-886 carboxylic acid 3-Methoxyquinoxalin-2- 586 1.5 6.6 856 carboxylic acid Acid 1-Benzofuran-2- 587 1.2 6.8 814 carboxylic acid 6-Ethyl-5-oxothiomorpholine- 588 1.4 5.8 841 3-carboxylic acid TABLE 6 (CONTINUED) 589 2-Chloro-1-oxy-nicotinic acid 1.3 4.5 825 590 Oxo- (thien-2-yl) -acetic acid 1 .2 6.9 808 591 Oxo- (phenyl) -acetic acid 1.1 6.9 802 3- (2-Nitrophenyl) -2-oxo- 6.7 592 1.6 861 propionic acid 7.1 3- (1 // - lndol-3-yl) -2-oxo-593 1.5 8.1 855 propionic acid 6. 7 594 2-Oxo-3-phenyl-propionic acid 1.2 816 7.3 Acid (2E) -3- (1 lmidazoi-4- 595 1.0 4.9 790 il) -acid Acid (2E) -3- (1 ¿lndol-3-il) - 6.4 596 1.4 839 acrylic 6.7 3- (1, 3-Benzodioxol-5-597 1.4 6.8 842 il) prop-2-enoic acid Acid (2E) -3-Quinolin-3-yl-598 1.5 6.2 851 acrylic Acid (2E) -3-Quino! In-2-il- 599 1.5 6.2 851 acrylic Acid (Quinoxaün-2-ilsulfanii) - 00 1.6 6.7 872 acetic TABLE 6 (CONTINUED) PHARMACEUTICAL EXAMPLES Tablets mg / tab Active ingredient 320 Lactose 150 Ethylcellulose 20 Sodium lauryl sulfate 7 Magnesium stearate 3 Tablet core 500 The active ingredient and the lactose are mixed together, and then granulated using water as the granulation fluid. The dried granules are mixed with ethyl cellulose, sodium lauryl sulfate and magnesium stearate, and the core of the tablet is formed using a suitable punch. The tablet can be coated using conventional techniques and coatings.

Invention The sterile containers were filled with the sterile active ingredient (500 mg). The main space of the container must be purged with sterile nitrogen; Containers should be closed using reinforced rubber and metal seals. The product can be reconstituted by dissolving it in injectable water (10 ml), or another sterile vehicle suitable for injection shortly before administration.

Activity data The MIC value (concentration for microbial inhibition), obtained according to the NCCLS (National Committee for Clinical Laboratory Standards), of the preferred compounds of the invention against Streptococcus pneumon / ae and Streptococcus pyogenes susceptible to erythromycin, are lower that or equal to 1 μ9 ???. In particular, examples 70, 56, 54, 49, 51, 58, 75, 66, 47, 52 and 17 showed a MIC < = 0.1 μgIp ^ \ against strains of Streptococcus pneumonJae susceptible to erythromycin. In addition, examples 70, 56, 54, 49, 51, 58, 75, 66, 47, 52 and 17 showed a MIC on the scale of < = 8 - 0.06 μ? /? T ?? against strains of Streptococcus pneumon / ae resistant to erythromycin.

Claims

NOVELTY OF THE INVENTION CLAIMS 1 .- A compound of formula (I): characterized in that: R is hydrogen, cyano, (CH2) nA-X-R4 or (CH2) nR5; A is a group selected from -N (R6) -, -N [C (0) Rs] -, -N (R6) C (0) -, -N (R6) S (0) 2-, -N ( R6) C (0) 0-, -N = C (R6) - or -N (R6) C (Y) N (R7) -; is C3 6 alkyl or alkenyl; R2 is hydrogen or a hydroxyl protecting group; R3 is hydrogen or halogen; X is a bond, a C1-10 alkylene chain, a C2_10 alkenylene chain or a C2-10 alkynylene chain, wherein said chains are: i) optionally interrupted by a bivalent radical selected from -O-, - N (R8) -, -C (O) -, -N (R8) C (Y) N (R9) -, -S (0) m-, -N (R8) C (0) -, -C ( 0) N (R8) -, -N (R8) C (0) C (0) -, -C (0) 0- or -C (NOR6) - and / or ii) optionally substituted by one or two selected groups of: C 1-4 alkyl, oxo, Ci-4 alkoxy, halogen, cyano, phenoxy, hydroxy, NRgRg, N (R 8) C (0) Rg, = NOR 6, NRgC (Y) NR 9 or optionally substituted phenyl; R4 is selected from: hydrogen, optionally substituted phenyl, optionally substituted C3_7 cycloalkyl, optionally substituted 9 to 10 membered bicyclic carbocyclic, optionally substituted 5 or 6 membered heteroaryl, wherein the 5-membered heteroaryl contains at least one heteroatom selected from oxygen, sulfur or nitrogen, and the 6-membered heteroaryl group contains from 1 to 3 nitrogen atoms, optionally substituted 5 to 6-membered heterocyclic, or R4 is an optionally substituted 9- or 10-membered fused bicyclic heterocyclic, having at least one heteroatom selected from oxygen, sulfur or nitrogen; R5 is a 5- or 6-membered heterocyclic containing at least one nitrogen, optionally substituted by one or two groups selected from oxo or fused bicyclic 9 or 10 membered heterocyclic having at least one heteroatom selected from oxygen, sulfur or nitrogen; R6 and R7 are independently hydrogen, d.4 alkyl or phenyl, which is optionally substituted by one or two C1-4 alkyl groups; R8 and R9 are independently hydrogen, phenyl (which can be substituted by 1 or 2 Ci-4 alkyl groups), or Rs and g are independently Ci-4 alkyl, which is optionally substituted by 1 or 2 groups selected from: phenyl, CM alkoxy, cyano, 5-membered heteroaryl containing 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, or the 6-membered heteroaryl group containing from 1 to 3 nitrogen atoms, hydroxy, oxo, carboxy; And it is an atom of oxygen or sulfur; n is 0 or an integer from 1 to 3; m is 0, 1 or 2; and pharmaceutically acceptable salts and solvates thereof. 2. The compound according to claim 1, further characterized in that R is (CH2) nA-X-R4 or (CH2) nR5. 3. The compound according to claim 1 or 2, further characterized in that Ri is methyl or 2-propenyl. 4. The compound according to any of claims 1 to 3, further characterized in that R2 is hydrogen. 5. The compound according to any of claims 1 to 4, further characterized in that R3 is hydrogen or fluorine. 6. The compound according to any of claims 1 to 5, further characterized in that A is selected from -NH-, -NHC (0) - or -NHC (Y) NH-. 7. The compound according to any of claims 1 to 6, further characterized in that X is an alkylene chain of C -4, which is optionally interrupted by a bivalent radical selected from -O-, -NH-, - C (O) -, -NHC (O) -, -S (0) 2- -S-, and / or said alkylene chain of Ci-4 is optionally substituted by a group selected from NH2, Ci-4 alkyl , oxo or -N-OH. 8. The compound according to any of claims 1 to 7, further characterized in that R4 is phenyl (optionally substituted by 1 to 3 groups which may be the same or different selected from nitro, amino, methyl, Ci-4 alkoxy ( that is, methoxy or hydroxy), 1-imidazolyl (optionally substituted by 1 to 3 groups which may be the same or different selected from pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, phenyl, m-nitrophenyl, dichlorophenyl, alkyl from CM ( that is, methyl, trifluoromethylphenyl, thiophen-2-yl, thiazo! -2-yl), 3-trifluoromethylpyrazol-4-yl, 1-pyrazolyl (optionally substituted by 1 to 3 groups which may be the same or different selected from halogen ( ie, chlorine, fluorine), pyridin-2-yl, pyridin-4-yl, quinolin-2-yl, quinolin-4-yl, quinoxalin-2-yl, pyrimidin-4-yl, Ci-4 alkyl ( that is, methyl, 1,3-benzooxazol-2-yl, p-chloro phenyl, difluoro phenyl, pyrazin-2-yl thiazol-5-yl, 1 H-indof-3-yl, 1 H-indol-2-yl , 3-rnetoxy-quinoxalin-2-yl, 2-quinolyl, 3-quinolinyl, 4-quinolinyl, 4-pyridinyl, 3-pyridinyl (optionally substituted by an amino), 5-methyl-furan-2-yl, 3 -thiophenyl, 6-methoxy-7H-purin-7-yl, quinoxaIin-2-yl, 3-methoxy quinoxal'n-2-yl, 6-methoxy-2-oxo-1,3-benzoxazol-3 (2H) -ilo, 1 H- pyrrolo [2,3-b] pyridin-1-yl, 2- (methylthio) -1 H -benzimidazol-1-yl, 1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl, 6 -methoxy-2-oxo-1,3-benzoxazol-3 (2H) -yl, 3H-imidazo [4,5-b] pyridin-3-yl, 1,3-benzoxazol-2-yl, benzothiazole-2- ilo, 1,3-benzo [1,3] dioxolyl, 3- (5-cyano-3,4-dimethylthien-2-yl) -1 H-1, 2,4-triazol-1-yl, 2,3- dihydro-benzo [1,4] dioxin-6-yl, 2,4-dimethyl-1,3-thiazol-5-yl or 4-oxo-4,5,6,7-tetrahydro-benzo [b] thiophene- 2-i 9. The compound according to any of claims 1 to 8, further characterized in that Ri is methyl, R2 or R3 is hydrogen, A is -NH-, -NHC (O) -, X is the alkylene chain of Ci- 4, which is optionally interrupted by a bivalent radical selected from -O-, -NH-, -C (O) -, -NHC (O) -, -S (0) 2- -S- and / or said chain of Ci-4 alkylene is optionally substituted by a group selected from NH2, C1.4 alkyl, oxo or N-OH, R4 is a group selected from 4- (pyridin-3-yl) -imidazol-1-yl, 4- (pyridin-3-yl) -imidazol-1-yl, quinoxalin-2-yl, quinoxalin-2-yl, quinolin-4-yl, quinoxalin-2-yl, - (2,3-dihydro-benzo [ 1, 4] dioxin-6-yl, 4-oxo-4,5,6,7-tetrahydro-benzo [b] thiophen-2-yl, 4-methoxy-3-n-phenyl-2, droxy-4,5-dimethoxy-phenyl, 3-hydroxy-4-methoxy-phenyl, 3,4-dimethoxy-phenyl, 4-hydroxy-3-methoxy-phenyl, 3-methoxy-quinoxalin-2-yl, 3 -amino-4-methoxy-phenyl, 4- (pyridin-3-yl) -imidazol-1-yl, quinolin-4-yl, 4-pyrimidin-4-yl-pyrazol-1-yl, 2- (methylthio) -1 H-benzimidazole- 1-yl, - [3- (4-chlorophenyl) -1 H -pyrazol-5-yl] propylamino) -methylene], 6-methoxy-2-oxo-1,3-benzoxazol-3 (2H) -yl, 1 H-pyrrolo [2,3-b] pyridin-1-yl, 3- (2,4-dimethyl-1,3-thiazol-5-yl) -1 H-pyrazole-1-yl, 4- phenyl-1 H-imidazol-1-yl, 4-pyridin-4-yl-1 H-imidazol-1-yl, thiophen-2-yl, 3- (5-cyano-3,4-dimethylthien-2-yl) ) -1 H-1, 2,4-triazol-1-yl, quinolin-3-yl, 1,3-thiazol-2-yl, and n is 0 or 1. 10. Compounds characterized in that they are selected from : (1 1 S, 21 S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12, 11 - [oxycarbonyl- (2- (4- (pyridin-3- il) -imidazol-1-yl) -ethylamino) -methylene] -erythromycin A; (1 1 S, 21 S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11 - [oxycarbonyl- (2- (quinolin-4-yl) -ethylamino) - methylene] -erythromycin A; (11 S, 21 S) -3-decladinosyl-11, 12-d / desox / -6-0-methyl-3-oxo-12,1 - [oxycarbonyl- (3- (4- (pyridin-3-yl) ) -imidazole-1-H propylamino) -methylene] -erythromycin A; (11S, 21 S) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-2,11- [ oxycarbonyl- (2- (quinoxalin-2-ylsulfanyl) -acetamido) -methylene] -erythromycin A; (1 1S, 21S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo- 12, 1 - [oxycarbonyl - ((4- (2,3-dihydro-benzo [1,4] dioxin-6-yl) -4-oxo) -butramide) -methylene] -erotriac Na A; (1 1 S, 21S) -3-decladinosl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (4- (4-methoxy-3 -nitro-phenyl) -4-oxo-butyramido) -metholene] -erythromycin A; (1 S, 21 S) -3-decladinosyl-1 1, 12-d-deoxy-6-0-methyl- 3-oxo-12,11- [oxycarbonyl- (4- (2-hydroxy-4,5-dimethoxy-pheny!) -4-oxo-butyramido) -methylene] -erythromycin A; (11S, 21S ) -3-decladinosyl-11, 12-dideoxy-6-0-methyl-3-oxo-12,1 1- [oxycarbonyl- (4- (4-oxo-4,5,6,7-tetrahydro-benzo [ b] thiophen-2-yl) -4-oxo-butyramide) -methylene] -ertromethine A; (11S, 21S) -3-decidnosyl-1,12-dideoxy-6- 0-methyl-3-oxo-12,11- [oxocarbonyl- (3- (4-quinol-2-i! -1-pyrazol-1-yl) propylamino) -methylene] - Erythromycin A; (11S, 21S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,11- [oxycarbonyl- (4- (3,4-dimethoxy-phenyl) -4- oxo-butyramido) -methylene] -erythromycin A; (1 1 S, 21 S) -3-decladinosyl-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1- [oxocarbonyl- (4- (4-hydroxy-3 -methoxy-phenyl) -4-oxo-butyramido) -methylene] -erithromycin A; and (11 S, 21 S) -3-decidinosil-1 1, 12-dideoxy-6-0-methyl-3-oxo-12,1- [oxocarbonyl- (3- (4- ( thiophen-2-yl) -imidazol-1-yl) -propylamino) -metholene] -erythromycin A. 1 1.- A process for the preparation of a compound of formula (I) , characterized in that it comprises: a) reacting a compound of formula (II): (II) (??) wherein R- ?, R2, R3 have the meanings defined in claim 1, Rn is a cladinose derivative of formula (II), wherein R2a is hydroxy, or hydroxy protecting group, R12 is hydrogen, or Rn together with R12, is an oxygen atom, with a suitable activated derivative of the acid (IV), HOC (0) XR4 (IV), or with a suitable activated derivative of the sulfonic acid (V) HOS (0) ) 2XR4 (V), respectively, wherein R4 and X have the meanings defined in claim 1, to give a compound of formula (I), wherein R is (CH2) nA-X-R4, A is -N ( R6) C (0) - or -N (R6) S (0) 2-, and X and n have the meanings defined in claim 1; b) reacting a compound of formula (II) with a compound of formula R4XN (R7) C (Y) L (VI), wherein L is a suitable leaving group, R6 is phenyl or C1-4 alkyl, R4 and X have the meanings defined in claim 1, to give a compound of formula (I), wherein R is (CH2) nA-X-R4, A is -N (R6) C (Y) N (R7) -, and X and n have the meanings defined in claim 1; c) reacting a compound of formula (II) with a compound of formula R4XN = C (Y) (VII), wherein R4 and X have the meanings defined in claim 1, to give a compound of formula (I), wherein R is (CH2) nA-X-R4, A is -N (R6) C (Y) NH-, and X and n have the meanings defined in claim 1; d) reacting a compound of formula (II) with a compound of formula R4XL (VIII), wherein R4 and X have the meanings defined in claim 1 and L is a suitable leaving group, to give a compound of formula (I) ), wherein R is (CH2) nA-X-R4, A is -N (R6) -, and X and n have the meanings defined in claim 1; e) reacting a compound of formula (II) with a compound of formula R4XOC (0) L (IX), wherein L is a suitable leaving group such as halogen (e.g., chlorine or bromine), R4 and X have the meanings defined in claim 1, to give a compound of formula (I), wherein R is (CH2) nA-X-R4, A is N (R6) C (0) 0, and X and n have the meanings defined in claim 1; f) reacting a compound of formula (II) with a compound of formula R4XCHO (X), wherein R4 and X have the meanings defined in the claim, to give a compound of formula (I), wherein R is (CH2) ) nA-X-R4, A is N = C (R6), and X and n have the meanings defined in claim 1; g) reacting a compound of formula (XI), wherein Rn and R12 have the meanings defined for compounds of formula (II), wherein R- ?, R2, R3 and 4 have the meanings defined in claim 1, with a compound of formula RsCOOH (Xla), (XI) to give a compound of formula (I), wherein R is (CH2) nA-X-R4, A is N = C (R6), and X and n have the meanings defined in claim 1; h) decarboxylation of a compound of formula (XII), wherein R 2 and R 3 have the meanings defined in claim 1, and R n and R 12 have the defined meanings for the compounds of formula (II), to give a compound of formula (I), wherein R is hydrogen; i) cyclization of chlorine derivatives (XIII), wherein R-i, R2 and R3 have the meanings defined in claim 1, and Rn and R12 have the defined meanings for the compounds of formula (II), (XIII) to give a compound of formula (I), wherein R is cyano; I) reacting a compound of formula (XVII), wherein R- ?, R2 and R3 have the meanings defined in claim 1, R and R12 have the meanings defined in formula (I), and R13 is C1 alkyl -4j with an aldehyde of formula: (XVII) (XVIII) wherein f¾, X and n have the meanings defined in claim 1, to give a compound of formula (I), wherein R is (CH 2) nAXR 4, and A and X have the meanings defined in claim 1; and n is an integer of 2 or 3; m) reacting a compound of formula (I), wherein Ri has the meanings defined in claim 1, R3 is hydrogen, and R2 is a hydroxy protecting group, with a halogenation agent, to give a compound of formula ( I), where R3 is halogen; n) cyclization of a compound of formula (XXXII), wherein L is a suitable leaving group such as halogen (ie, chlorine or bromine), Ri, R2, R3 have the meanings defined in claim 1, Rn and Ri2l have the meaning defined in formula (II), X is C4-5 alkylene chain optionally substituted by one or two groups selected from oxo, fused bicyclic 9 or 10 membered heterocyclic having at least one heteroatom selected from oxygen, sulfur or nitrogen, (XXXII) to give a compound of formula (I), wherein Ri is (CH2) nR5, 'and then, if required, subjecting the resulting compound to one or more of the following operations: i) hydrolysis of the cyiadinium derivative (III); ii) conversion of the 3-hydroxy group into the 3-oxo; iii) removal of the protective group R2, and iv) conversion of the resulting compound of formula (II) into pharmaceutically acceptable salts and solvates thereof. 12 - The use of a compound as claimed in any of claims 1 to 10, in the preparation of a medicament for use in the therapy of systemic or topical bacterial infections in the body of a human or animal. 13. The use of a compound as claimed in any of claims 1 to 10, for use in the preparation of a medicament for the treatment or prophylaxis of systemic or topical bacterial infections in the body of an animal or human. 14. - A pharmaceutical composition, characterized in that it comprises a compound according to any of claims 1 to 10, in admixture with one or more pharmaceutically acceptable vehicles or excipients. SUMMARY OF THE INVENTION The present invention relates to ketones of 11, 12 and lactone of formula (I): (I) wherein: R is hydrogen, cyano, (CH2) nA-X-R4 or (CH2) nR5; A is a group selected from -N (R6) - -N [C (0) R6] - -N (R6) C (0) -, -N (R6) S (0) 2- - N (R6) C (0) 0-, -N = C (R6) - or -N (R6) C (Y) N (R7) -; Ri is C ^ 6 alkyl or alkenyl; R2 is hydrogen or a hydroxyl protecting group; R3 is hydrogen or halogen; X is a bond, a C1-10 alkylene chain, a C2-10 alkenylene chain or an alkynylene chain of C2 wherein said chains are: i) optionally interrupted by a bivalent radical selected from -O-, -N (R8) -C (O) -, -N (R8) C (Y) N (R9) -S (0) m-, -N (R8) C (0) -C (0) N ( R8) - -N (R8) C (0) C (0) -C (0) 0- or -C (NOR6) - and / or ii) optionally substituted by one or two groups selected from: d- alkyl 4, oxo, C1-4 alkoxy, halogen, cyano, phenoxy, hydroxy, NR8Rg, N (R8) C (0) R9, = N0R6, NR8C (Y) NRg or phenyl optionally substituted; R4 is selected from: hydrogen, optionally substituted phenyl, optionally substituted U3-7 cycloalkyl, optionally substituted 9 to 10 membered bicyclic carbocyclic, optionally substituted 5 or 6 membered heteroaryl, wherein the 5-membered heteroaryl contains at least a heteroatom selected from oxygen, sulfur or nitrogen, and the 6-membered heteroaryl group contains from 1 to 3 nitrogen atoms, optionally substituted 5 to 6-membered heterocyclic, or R4 is an optionally substituted 9- or 10-membered bicyclic heterocyclic, having at least one heteroatom selected from oxygen, sulfur or nitrogen; R5 is a 5- or 6-membered heterocyclic containing at least one nitrogen, optionally substituted by one or two groups selected from oxo or fused bicyclic 9 or 10 membered heterocyclic having at least one heteroatom selected from oxygen, sulfur or nitrogen; R6 and R7 are independently hydrogen, C1-4 alkyl or phenyl, which is optionally substituted by one or two C1-4 alkyl groups; Re and R9 are independently hydrogen, phenyl (which can be substituted by 1 or 2 Ci-4 alkyl groups), or Re and R9 are independently Ci-4 alkyl, which is optionally substituted by 1 or 2 groups selected from : phenyl, Ci-4 alkoxy, cyano, 5-membered heteroaryl containing 1 or 2 heteroatoms selected from oxygen, sulfur or nitrogen, or the 6-membered heteroaryl group containing from 1 to 3 nitrogen atoms, hydroxy,